Pyrazolopyridine sulfonamides as nematicides

ABSTRACT

Disclosed are compounds of formula (I) which possess nematicidal properties 
     
       
         
         
             
             
         
       
     
     wherein the structural elements have the meaning as indicated in the description.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a divisional application of U.S. patent applicationSer. No. 15/309,183, filed 6 Nov. 2016, which is a § 371 National StageApplication of PCT/EP2015/059776, filed 5 May 2015, which claimspriority to EP 14167534.8, filed 8 May 2014. The above applications areeach incorporated by reference in their entireties.

BACKGROUND Field of the Invention

The present invention relates to pyrazolopyridine sulfonamides, theiruse for the control of animal pests, especially nematodes, inagricultures, formulations containing such compounds and methods for thecontrol of animal pests, especially nematodes. This invention relates tocertain sulfonamides, their N-oxides, salts and formulations suitablefor agronomic and nonagronomic uses, and methods of their use forcontrolling animal pests, especially nematodes, in both agronomic andnonagronomic environments. The present invention further relates toprocesses and intermediate compounds for the preparation of suchpyrazolopyridine sulfonamides.

Description of Related Art

Nematodes cause a substantial loss in agricultural product includingfood and industrial crops and are combated with chemical compoundshaving nematicidal activity. To be useful in agriculture these compoundsshould have a high activity, a broad spectrum activity against differentstrains of nematodes and should not be toxic to non-target organisms.Due to widespread development of resistance to anthelmintic agents innematode parasites, nematodes continue to cause problems in livestockdespite the available chemical therapeutic agents. The need continuesfor new compounds which are more effective, less costly, less toxic,environmentally safer or have different modes of action.

European Patent Application Publication No. 0 244 166 A2 (referred to asP1) discloses compounds of formula (i) as herbicides

wherein, inter alia, R is H or an organic substituent, W is O or S, L isan aryl or heteroaryl moiety, and A is selected from a list of bi-, tri-and quadricyclic heterocyclic groups.

PCT patent application publication WO 2010/129500 (P2) disclosescompounds of formula (ii) (including all stereoisomers), N-oxides, andsalts thereof, and compositions containing them and their use forcontrolling a parasitic nematode:

wherein, interalia, Z is O or S and Q is phenyl, naphthalenyl, a 5- or6-membered hetero-aromatic ring or an 8- to 10-membered heteroaromaticbicyclic ring system, each optionally substituted with 1 to 5substituents.

Anonymously disclosed publication IP com Journal 10, 26 (2010) (P3)describes 10 explicitly listed compounds of general formula (ii) inmixtures with various insecticides in several mixture ratios.

PCT Patent Application Publication WO 2012/054233 (P4) disclosescompounds of formula (iii) (including all stereoisomers), N-oxides, andsalts thereof, and compositions containing them and their use forcontrolling a parasitic nematode:

wherein, interalia, Z is O or S, Q is phenyl, naphthalenyl, a 5- or6-membered heteroaromatic ring or an 8- to 10-membered heteroaromaticbicyclic ring system, each optionally substituted with 1 to 5substituents and A¹, A², A³ and A⁴ are independently N or CR¹, providedthat only one of A¹, A², A³ and A⁴ is N.

PCT Patent Application Publication WO 2013/055584 (P5) discloses solidforms of a certain nematocidal imidazopyridine sulfonamide of formula(ii).

The compounds of the present invention are not disclosed in thesepublications.

It is an object of the present invention to provide compounds which canbe used as nematicides with a satisfactory or improved nematicidalactivity, particularly at relatively low application rates, with a highselectivity and high compatibility in crop-plant cultures.

SUMMARY OF THE INVENTION

This invention is directed to compounds of formula (I) (including allstereoisomers), N-oxides, and salts thereof, and formulations containingthem and their use for controlling animal pests, especially nematodes,especially parasitic nematodes:

wherein

-   -   Z is O or S;    -   each R¹ is independently H, halogen, cyano, nitro, SF₅, OCN,        SCN, Si(R¹⁵)₃, OR⁴, NR⁵R⁶, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², OC(O)R⁷, OC(O)OR⁸, OC(O)NR¹¹R¹², OS(O)₂R⁹,        OS(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹ or        N(R¹⁰)S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano,        nitro, OR⁴, NR⁵ R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ and        S(O)₂NR¹¹R¹²;        or phenyl, naphthalenyl or a 5- or 6-membered heteroaromatic        ring, each optionally substituted with 1 to 5 substituents        independently selected from the group consisting of halogen,        cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl,        C₂-C₄-alkynyl, C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ and S(O)₂NR¹¹R¹²;    -   R² is H, halogen, cyano, nitro, SF₅, OCN, SCN, Si(R¹⁵)₃, OR⁴,        NR⁵R⁶, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,        C₃-C₇-cycloalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², OC(O)R⁷, OC(O)OR⁸, OC(O)NR¹¹R¹², OS(O)₂R⁹,        OS(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹ or        N(R¹⁰)S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano,        nitro, OR⁴, NR⁵ R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ and        S(O)₂NR¹¹R¹²;    -   or phenyl, naphthalenyl or a 5- or 6-membered heteroaromatic        ring, each optionally substituted with 1 to 5 substituents        independently selected from the group consisting of halogen,        cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl,        C₂-C₄-alkynyl, C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ and S(O)₂NR¹¹R¹²,        C₂-C₆-alkoxyalkyl, OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);    -   R³ is H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl or        C₅-C₇-cycloalkenyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, nitro, OR^(4a), and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano,        nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ and        S(O)₂NR¹¹R¹²;    -   or C₁-C₆-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of phenyl or a        5- or 6-membered heteroaromatic ring, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶,        C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-haloalkyl,        C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and        N(R¹⁰)C(O)R^(7a);    -   or phenyl optionally substituted with 1 to 5 substituents        independently selected from the group consisting of halogen,        cyano, nitro, OR⁴, NR⁵ R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl,        C₂-C₄-alkynyl, C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl,        C₂-C₆-alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);    -   Q is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,        C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl, phenyl, naphthalenyl or        a 5- or 6-membered heteroaromatic ring or an 8- to 10-membered        heteroaromatic bicyclic ring system, each optionally substituted        with 1 to 5 substituents independently selected from the group        consisting of halogen, cyano, nitro, SF₅, OCN, SCN, Si(R¹⁵)₃,        OR⁴, NR⁵R⁶, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C(X)R⁷,        C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R⁷,        OC(O)OR⁸, OC(O)NR¹¹R¹², OS(O)₂R⁹, OS(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷,        N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹, N(R¹⁰)S(O)₂NR¹¹R¹² and R¹⁴;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123):

-   -   wherein each R^(v) is independently any substituent as defined        in the Summary of the Invention for R¹, R², R³ and r is 0, 1, 2,        3, 4 or 5, limited by the number of available positions on each        U group;    -   each R⁴ is independently H, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl or        C₂-C₆-haloalkynyl;    -   or C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, each substituted        with 1 to 4 substituents independently selected from the group        consisting of, cyano, nitro, OR^(4a), NR^(5a)R^(6a), C(X)R^(7a),        C(O)OR^(8a), C(O)NR¹¹R¹², S(O)_(m)R^(9a) and S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or phenyl optionally substituted with 1 to 3 substituents        independently selected from the group consisting of halogen,        cyano, nitro, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C(X)R^(7a), C(O)OR^(8a),        C(O)NR¹¹R¹², OR^(4a), C₂-C₆-alkoxyalkyl, S(O)_(m)R^(9a),        S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);    -   each R^(4a) is independently H, C₁-C₆-alkyl or C₁-C₆-haloalkyl;    -   each R⁵ is independently H, NR^(5a)R^(6a), C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,        S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or phenyl optionally substituted with 1 to 3 substituents        independently selected from the group consisting of halogen,        cyano, nitro, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C(X)R^(7a), C(O)OR^(8a),        C(O)NR¹¹R¹², OR^(4a), C₂-C₆-alkoxyalkyl, S(O)_(m)R⁹a,        S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);    -   each R^(5a) is independently H or C₁-C₆-alkyl;    -   each R⁶ is independently H, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl or        C₂-C₆-haloalkynyl;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   each R^(6a) is independently H, C₁-C₆-alkyl, C(O)R¹³ or        C(O)OR¹³;    -   each R⁷ is independently H, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl or        C₂-C₆-haloalkynyl;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or phenyl optionally substituted with 1 to 3 substituents        independently selected from the group consisting of halogen,        cyano, nitro, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C(X)R^(7a), C(O)OR^(8a),        C(O)NR¹¹R¹², OR^(4a), C₂-C₆-alkoxyalkyl, S(O)_(m)R^(9a),        S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);    -   each R^(7a) is independently C₁-C₆-alkyl or C₁-C₆-haloalkyl;    -   each R⁸ is independently H, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl or        C₂-C₆-haloalkynyl;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, each substituted        with 1 to 4 substituents independently selected from the group        consisting of, cyano, nitro, OR^(4a), NR^(5a)R^(6a), C(X)R^(7a),        C(O)OR^(8a), C(O)NR¹¹R¹², S(O)_(m)R^(9a) and S(O)₂NR¹¹R¹²;    -   or phenyl optionally substituted with 1 to 3 substituents        independently selected from the group consisting of halogen,        cyano, nitro, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C(X)R^(7a), C(O)OR^(8a),        C(O)NR¹¹R¹², OR^(4a), C₂-C₆-alkoxyalkyl, S(O)_(m)R^(9a),        S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);    -   each R^(8a) is independently C₁-C₆-alkyl or C₁-C₆-haloalkyl;    -   each R⁹ is independently H, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl or        C₂-C₆-haloalkynyl; or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, each substituted        with 1 to 4 substituents independently selected from the group        consisting of, cyano, nitro, OR^(4a), NR^(5a)R^(6a), C(X)R^(7a),        C(O)OR^(8a), C(O)NR¹¹R¹², S(O)_(m)R^(9a) and S(O)₂NR¹¹R¹²;    -   or phenyl optionally substituted with 1 to 3 substituents        independently selected from the group consisting of halogen,        cyano, nitro, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C(X)R^(7a), C(O)OR^(8a),        C(O)NR¹¹R¹², OR^(4a), C₂-C₆-alkoxyalkyl, S(O)_(m)R^(9a),        S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);    -   each R^(9a) is independently C₁-C₆-alkyl or C₁-C₆-haloalkyl;    -   each R¹⁰ is independently H, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C₃-C₇-cycloalkyl, C(X)R^(7a), C(O)OR^(8a),        C(O)NR¹¹R¹², S(O)_(m)R^(9a) or S(O)₂NR¹¹R¹²;    -   each R¹¹ is independently H, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl or        C₂-C₆-haloalkynyl;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, each substituted        with 1 to 4 substituents independently selected from the group        consisting of, cyano, nitro, OR^(4a), NR^(5a)R^(6a), C(X)R^(7a),        C(O)OR^(8a), C(O)NR^(11a)R¹², S(O)_(m)R^(9a) and        S(O)₂NR^(11a)R¹²;    -   or phenyl optionally substituted with 1 to 3 substituents        independently selected from the group consisting of halogen,        cyano, nitro, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C(X)R^(7a), C(O)OR^(8a),        C(O)NR^(11a)R¹², OR^(4a), C₂-C₆-alkoxyalkyl, S(O)_(m)R^(9a),        S(O)₂NR^(11a)R¹², NR^(5a)R^(6a), OC(O)R^(7a) and        N(R¹⁰)C(O)R^(7a);    -   each R^(11a) is independently H, C₁-C₆-alkyl, C₂-C₆-alkenyl or        C₂-C₆-alkynyl;    -   each R¹² is independently H, NR^(5a)R^(6a), C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,        S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or phenyl optionally substituted with 1 to 3 substituents        independently selected from the group consisting of halogen,        cyano, nitro, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C(X)R^(7a), C(O)OR^(8a),        C(O)NR¹¹R¹², OR^(4a), C₂-C₆-alkoxyalkyl, S(O)_(m)R^(9a),        S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);    -   each R¹³ is independently H, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl or        C₂-C₆-haloalkynyl;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   each R¹⁴ is independently C₃-C₇-cycloalkyl,        C₄-C₈-cycloalkylalkyl, C₆-C₁₄-cycloalkylcycloalkyl or        C₅-C₇-cycloalkenyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and        S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, each substituted        with 1 to 4 substituents independently selected from the group        consisting of cyano, nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ and S(O)₂NR¹¹R¹²;    -   or phenyl, naphthalenyl or a 5- or 6-membered heteroaromatic        ring, each optionally substituted with 1 to 5 substituents        independently selected from the group consisting of halogen,        cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄₋alkyl, C₂-C₄-alkenyl,        C₂-C₄-alkynyl, C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl,        C₂-C₆-alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and        N(R¹⁰)C(O)R^(7a);    -   each R¹⁵ is independently C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl or        C₂-C₆-haloalkynyl; or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl or        C₅-C₇-cycloalkenyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and        S(O)_(m)R^(9a);    -   or phenyl optionally substituted with 1 to 5 substituents        independently selected from the group consisting of halogen,        cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl,        C₂-C₄-alkynyl, C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl,        C₂-C₆-alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);    -   X is O or S;    -   each m is independently 0, 1 or 2;    -   and n is 0, 1, 2, 3 or 4.

Compounds of the present invention can exist in one or more optical orchiral isomer forms depending on the number of asymmetric centres in thecompound. The invention thus relates equally to all the optical isomersand to their racemic or scalemic mixtures (the term “scalemic” denotes amixture of enantiomers in different proportions) and to the mixtures ofall the possible stereoisomers, in all proportions. The diastereoisomersand/or the optical isomers can be separated according to the methodswhich are known per se by the man ordinary skilled in the art.

Compounds of the present invention can also exist in one or moregeometric isomer forms depending on the number of double bonds in thecompound, especially all syn/anti (or cis/trans) isomers and to allpossible syn/anti (or cis/trans) mixtures. The invention thus relatesequally to all geometric isomers and to all possible mixtures, in allproportions. The geometric isomers can be separated according to generalmethods, which are known per se by the man ordinary skilled in the art.

Compounds of formula (I) may be found in its tautomeric form resultingfrom the shift of the proton of a hydroxy, sulfanyl or amino group. Suchtautomeric forms of such compounds are also part of the presentinvention. More generally speaking, all tautomeric forms of compounds offormula (I), as well as the tautomeric forms of the compounds which canoptionally be used as intermediates in the preparation processes andwhich will be defined in the description of these processes, are alsopart of the present invention.

Further, this invention is also directed to N-oxides of the compounds offormula (I) (including all stereoisomers), and salts of the compounds offormula (I) (including all stereoisomers).

Further, this invention is directed to a formulation comprising acompound of formula (I), an N-oxide, or a salt thereof, and their usefor controlling an animal pest, especially a parasitic nematode, asdescribed above. This invention also provides a formulation comprising acompound of formula (I), an N-oxide, or a salt thereof. and at least oneextender and/or at least one surfactant. In one embodiment, thisinvention also provides a formulation in which a compound of formula(I), an N-oxide, or a salt thereof, is present in a mixture with atleast one other active compound, preferably a mixing partner asdescribed below.

This invention provides a method for controlling an animal pest,especially a parasitic nematode, in which a compound of formula (I), anN-oxide, or a salt thereof, or a a formulation described herein isallowed to act on the animal pest and/or their habitat. In such methods,a biologically effective amount of compound or formulation is applied.

This invention also provides a method for protecting a seed and/or agerminating plant from attack by a pest, particularly a parasiticnematode, comprising the step of contacting the seed with a compound offormula (I), an N-oxide, or a salt thereof, or with a formulationdescribed herein. In such methods, a biologically effective amount ofcompound or formulation is applied. This invention also relates to aseed which was obtained by such a method.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 depicts H-NMR spectrum ofN-amino-3-chloro-5-trifluoromethyl-pyridinium p-tosylate ([D₆]-DMSO, 400MHz).

FIG. 2 depicts H-NMR spectrum of dimethyl4-chloro-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2,3-dicarboxylate(CDCl₃, 400 MHz).

FIG. 3 depicts the H-NMR spectrum of4-chloro-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid(II-1) ([D₆]-DMSO, 400 MHz).

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

As used herein, the terms “comprises”, “comprising”, “includes”,“including”, “has”, “having”, “contains”, “containing”, “characterizedby” or any other variation thereof, are intended to cover anon-exclusive inclusion, subject to any limitation explicitly indicated.For example, a formulation, mixture, process or method that comprises alist of elements is not necessarily limited to only those elements butmay include other elements not expressly listed or inherent to suchformulation, mixture, process or method.

The transitional phrase “consisting of” excludes any element, step oringredient not specified. If in the claim, such would close the claim tothe inclusion of materials other than those recited except forimpurities ordinarily associated therewith. When the phrase “consistingof” appears in a clause of the body of a claim, rather than immediatelyfollowing the preamble, it limits only the element set forth in thatclause; other elements are not excluded from the claim as a whole.

The transitional phrase “consisting essentially of” is used to define aformulation or method that includes materials, steps, features,components or elements, in addition to those literally disclosed,provided that these additional materials, steps, features, components orelements do not materially affect the basic and novel characteristic(s)of the claimed invention. The term “consisting essentially of” occupiesa middle ground between “comprising” and “consisting of”.

Where applicants have defined an invention or a portion thereof with anopen-ended term such as “comprising”, it should be readily understoodthat (unless otherwise stated) the description should be interpreted toalso describe such an invention using the terms “consisting essentiallyof” or “consisting of”.

Further, unless expressly stated to the contrary, “or” refers to aninclusive or and not to an exclusive or. For example, a condition A or Bis satisfied by any one of the following: A is true (or present) and Bis false (or not present), A is false (or not present) and B is true (orpresent), and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element orcomponent of the invention are intended to be nonrestrictive regardingthe number of instances (i.e. occurrences) of the element or component.Therefore “a” or “an” should be read to include one or at least one, andthe singular word form of the element or component also includes theplural unless the number is obviously meant to be singular.

As used to in the present disclosure and claims, the term “nematode”refers to a living organism of the phylum Nematoda. As generallydefined, a “parasite” lives or grows inside or feeds on another livingorganism (such as a plant, animal or human) described as the “host”. Asreferred to in the present disclosure and claims a “parasitic nematode”is particularly a nematode that injures or damages tissue or causesother forms of disease in plants, animals (particularly vertebrates) orhumans.

A parasite “infestation” refers to the presence of parasites in numbersthat pose a risk to plants, humans or animals. The presence can be inthe environment, e.g., in a human or animal house, or surroundingproperty or structures, on an agricultural crop or other type of plant,in animal bedding, on the skin or fur of an animal, etc. When theinfestation that is referred to is within an animal, e.g., in the bloodor other internal tissues, the term infestation is also intended to besynonymous with the term, “infection,” as that term is generallyunderstood in the art, unless otherwise stated.

As referred to in the present disclosure and claims, the terms“parasiticidal” and “parasiticidally” refers to observable effects on aparasitic nematode to provide protection of a plant, animal or humanfrom the nematode. Parasiticidal effects typically relate to diminishingthe occurrence or activity of the target parasitic nematode. Sucheffects on the nematode include necrosis, death, retarded growth,diminished mobility or lessened ability to remain on or in the hostplant, animal or human, reduced feeding and inhibition of reproduction.These effects on parasitic nematodes provide control (includingprevention, reduction or elimination) of parasitic infestation orinfection of the plant, animal or human. Therefore “control” of aparasitic nematode means achieving a parasiticidal effect on thenematode. The expressions “parasiticidally effective amount” and“biologically effective amount” in the context of applying a chemicalcompound to control a parasitic nematode refer an amount of the compoundthat is sufficient to control the parasitic nematode. Likewise, theexpressions “parasiticidally effective amount” and “biologicallyeffective amount” in the context of applying a chemical compound tocontrol an animal pest refer an amount of the compound that issufficient to control the animal pest.

The term “agronomic” refers to the production of field crops such as forfood and fiber and includes the growth of soybeans and other legumes,cereal (e.g., wheat, oats, barley, rye, rice, maize/com), leafyvegetables (e.g., lettuce, cabbage, and other cole crops), fruitingvegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits),potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stoneand citrus), small fruit (berries, cherries) and other specialty crops(e.g., canola, sunflower, olives).

The term “nonagronomic” refers to other than field crops, such ashorticultural crops (e.g., greenhouse, nursery or ornamental plants notgrown in a field), residential, agricultural, commercial and industrialstructures, turf (e.g., sod farm, pasture, golf course, lawn, sportsfield, etc.), wood products, stored product, agro-forestry andvegetation management, public health (i.e. human) and animal health(e.g., domesticated animals such as pets, livestock and poultry,undomesticated animals such as wildlife) applications.

Nonagronomic applications include protecting an animal from a parasiticnematode by administering a parasiticidally effective (i.e. biologicallyeffective) amount of a compound of the invention, typically in the formof a formulation formulated for veterinary use, to the animal to beprotected.

In the above recitations, the term “alkyl”, used either alone or incompound words such as “haloalkyl” includes straight-chain or branchedalkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the differentbutyl, pentyl or hexyl isomers. “Alkenyl” includes straight-chain orbranched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and thedifferent butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includespolyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includesstraight-chain or branched alkynes such as ethynyl, 1-propynyl,2-propynyl and the different butynyl, pentynyl and hexynyl isomers.“Alkynyl” can also include moieties comprised of multiple triple bondssuch as 2,5-hexadiynyl.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy,isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.“Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of“alkoxyalkyl” include CH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂and CH₃CH₂OCH₂CH₂.

“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl. The term “cycloalkylalkyl” denotes cycloalkylsubstitution on an alkyl moiety. Examples of “cycloalkylalkyl” includecyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moietiesbonded to straight-chain or branched alkyl groups. “Cycloalkenyl”includes groups such as cyclopentenyl and cyclohexenyl as well as groupswith more than 10 one double bond such as 1,3- and 1,4-cyclohexadienyl.The term “cycloalkylcycloalkyl” denotes cycloalkyl substitution onanother cycloalkyl ring, wherein each cycloalkyl ring independently hasfrom 3 to 7 carbon atom ring members. Examples of cycloalkylcycloalkylinclude cyclopropylcyclopropyl (such as 1,1′-bicyclopropyl-1-yl,1,1′-bicyclopropyl-2-yl), cyclohexylcyclopentyl (such as4-cyclopentylcyclohexyl) and cyclohexylcyclohexyl (such as1,1′-bicyclohexyl-1-yl), and the different cis- andtrans-cycloalkylcycloalkyl isomers, (such as(1R,2S)-1,1′-bicyclopropyl-2-yl and (1R,2R)-1,1′-bicyclopropyl-2-yl).

The term “halogen”, either alone or in compound words such as“haloalkyl”, or when used in descriptions such as “alkyl substitutedwith halogen” includes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as “haloalkyl”, or when 20 used indescriptions such as “alkyl substituted with halogen” said alkyl may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “haloalkyl” or “alkyl substituted withhalogen” include F₃C, ClCH₂, CF₃CH₂ and CF₃CCl₂. The terms “haloalkoxy”,“haloalkenyl”, “haloalkynyl”, and the like, are defined analogously tothe term “haloalkyl”. Examples of “haloalkoxy” include CF₃O, CCl₃CH₂O,HCF₂CH₂CH₂O and CF₃CH₂O. Examples of “haloalkenyl” include (Cl)₂C═CHCH₂and CF₃CH₂CH═CHCH₂. Examples of “haloalkynyl” include HC≡CCHCl, CF₃C≡C,CCl₃C≡C and FCH₂C≡CCH₂.

The chemical abbreviation C(O) as used herein represents a carbonylmoiety. For example, C(O)CH₃ represents an acetyl group. The chemicalabbreviations CO₂ and C(O)O as used herein represent an ester moiety.For example, CO₂Me and C(O)OMe represent a methyl ester.

“OCN” means —O—C═N, and “SCN” means —S—C═N.

The total number of carbon atoms in a substituent group is indicated bythe “Cj-Cj” prefix where i and j are numbers from 1 to 14.C₂-alkoxyalkyl designates CH₃OCH₂; C₃-alkoxyalkyl designates, forexample, CH₃CH(OCH₃), CH₃OCH₂CH₂ or CH₃CH₂OCH₂; and C₄-alkoxyalkyldesignates the various isomers of an alkyl group substituted with analkoxy group containing a total of four carbon atoms, examples includingCH₃CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂.

When a compound is substituted with a substituent bearing a subscriptthat indicates the number of said substituents can exceed 1, saidsubstituents (when they exceed 1) are independently selected from thegroup of defined substituents, e.g., R¹, n is 0, 1, or 2. However, it isto be understood that n is limited by the maximum number of availablepositions to which the residue in question, e.g. R¹, can be bonded to.When a group contains a substituent which can be hydrogen, for exampleR² or R³, then when this substituent is taken as hydrogen, it isrecognized that this is equivalent to said group being unsubstituted.When a variable group is shown to be optionally attached to a position,for example (R^(v))_(r) in U-29 wherein r may be 0, then hydrogen may beat the position even if not recited in the variable group definition.When one or more positions on a group are said to be “not substituted”or “unsubstituted”, then hydrogen atoms are attached to take up any freevalency.

Unless otherwise indicated, a “ring” or “ring system” as a component offormula (I) (e.g., substituent Q) is carbocyclic or heterocyclic. Theterm “ring system” denotes two or more fused rings. The term“heterocyclic ring” denotes a ring in which at least one atom formingthe ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur.Typically a heterocyclic ring contains no more than 4 nitrogens, no morethan 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, aheterocyclic ring can be a saturated, partially unsaturated, or fullyunsaturated ring. The term “heterocyclic ring system” denotes a ringsystem in which at least one ring of the ring system is a heterocyclicring. Unless otherwise indicated, heterocyclic rings and ring systemscan be attached through any available carbon or nitrogen by replacementof a hydrogen on said carbon or nitrogen.

“Aromatic” indicates that each of the ring atoms is essentially in thesame plane and has a R-orbital perpendicular to the ring plane, and inwhich (4n+2) π electrons, where π is a positive integer, are associatedwith the ring to comply with Hückel's rule. When a fully unsaturatedheterocyclic ring satisfies Hückel's rule, then said ring is also calleda “heteroaromatic ring”. The term “heteroaromatic ring system” denotes aheterocyclic ring system in which at least one ring of the ring systemis aromatic.

As used herein, the following definitions shall apply unless otherwiseindicated. The term “optionally substituted” is used interchangeablywith the phrase “substituted or unsubstituted” or with the term“(un)substituted”. The expression “optionally substituted with 1 to 4substituents” means that no substituent is present (i.e. unsubstituted)or that 1, 2, 3 or 4 substituents are present (limited by the number ofavailable bonding positions). Unless otherwise indicated, an optionallysubstituted group may have a substituent at each substitutable positionof the group, and each substitution is independent of the other.

When a substituent is a 5- or 6-membered nitrogen-containingheteroaromatic ring, it may be attached to the remainder of formula (I)though any available carbon or nitrogen ring atom, unless otherwisedescribed.

An example of phenyl optionally substituted with one to fivesubstituents is the ring illustrated as U-1. Examples of furtheroptionally substituted 5- or 6-membered heteroaromatic ring include therings U-2 through U-61 wherein R^(v) is any substituent as defined inthe Summary of the Invention for R¹, R², R³ and r is an integer from 0to 4, limited by the number of available positions on each U group. AsU-29, U-30, U-36, U-37, U-38, U-39, U-40, U-41, U-42 and U-43 have onlyone available position, for these U groups r is limited to the integers0 or 1, and r being 0 means that the U group is unsubstituted and ahydrogen is present at the position indicated by (R^(v))_(r).

Further and as noted above, Q can also be (among others) an 8- to10-membered heteroaromatic bicyclic ring system optionally substitutedwith substituents selected from a group of substituents as defined inthe Summary of Invention. Examples of optionally substituted 8-, 9- or10-membered heteroaromatic bicyclic ring systems include the rings U-81through U-123 wherein R^(v) is any substituent as defined in the Summaryof the Invention for Q, and r is typically an integer from 0 to 4.

Although R^(v) groups are shown in the structures U-1 through U-123, itis noted that they do not need to be present since they are optionalsubstituents. The nitrogen atoms that require substitution to fill theirvalence are substituted with H or R^(v). Note that when the attachmentpoint between (R^(v))_(r) and the U group is illustrated as floating,(R^(v))_(r) can be attached to any available carbon atom or nitrogenatom of the U group. Note that when the attachment point on the U groupis illustrated as floating, the U group can be attached to the remainderof formula (I) through any available carbon or nitrogen of the U groupby replacement of a hydrogen atom. Note that some U groups can only besubstituted with less than 4 R^(v) groups (e.g., U-2 through U-5, U-7through U-48, and U-52 through U-61).

The compounds of the invention are defined in general terms by theformula (I). In the compounds of the invention,

each R¹ preferably is independently

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷,        N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹ or N(R¹⁰)S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, C(X)R⁷, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, each R¹ is independently

-   -   halogen, cyano, OR⁴, C₁-C₄-alkyl, C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

Especially preferably, each R¹ is independently

-   -   chlorine or trifluoromethyl.

R² preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,        C₃-C₇-cycloalkyl, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R² is

-   -   H, halogen, cyano, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of cyano, OR⁴        and S(O)_(m)R⁹.

Especially preferably, R² is hydrogen.

R³ preferably is

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C(X)R⁷,        C(O)OR⁸ or C(O)NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, OR^(4a) and        S(O)_(m)R^(9a);    -   or C₁-C₄-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        C(X)R⁷ and C(O)OR⁸;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of phenyl or a        5- or 6-membered heteroaromatic ring, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴,        C₁-C₄-haloalkyl, C₂-C₆-alkoxyalkyl, C(X)R⁷, C(O)OR⁸, S(O)_(m)R⁹        and S(O)₂NR¹¹R¹².

More preferably, R³ is

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl, C(X)R⁷ or C(O)OR⁸;    -   or C₁-C₂-alkyl substituted with OR⁴;    -   or C₁-C₂-alkyl substituted with phenyl.

Especially preferably, R³ is hydrogen.

Q preferably is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₃-C₇-cycloalkyl, phenyl or a 5- or 6-membered heteroaromatic        ring system, each optionally substituted with 1 to 5        substituents independently selected from the group consisting of        halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹² and R¹⁴;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

More preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₇-cycloalkyl, phenyl or a 5-        or 6-membered heteroaromatic ring system, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹ and        S(O)₂NR¹¹R¹²;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

Even more preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₃-C₇-cycloalkyl;    -   or Q is selected from the group consisting of (U-1) to (U-61)        and (U-103).

Especially preferably, Q is methyl, ethyl or cyclopropyl or is selectedfrom the group consisting of (U-1), (U-49) and (U-103), particularly(U-1).

Each R⁴ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen.

More preferably, each R⁴ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R⁴ is independently methyl, ethyl, propyl,isopropyl, difluoromethyl or trifluoromethyl.

Each R^(4a) preferably is independently

-   -   H, C₁-C₆-alkyl or C₁-C₆-haloalkyl.

More preferably, each R^(4a) is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R^(4a) is independently

-   -   methyl or ethyl.

Each R⁵ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl;        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁵ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹².

Especially preferably, each R⁵ is independently

-   -   H, methyl or ethyl.

Each R^(5a) preferably is independently

-   -   H or C₁-C₄-alkyl.

More preferably, each R^(5a) is independently

-   -   H or C₁-C₂-alkyl.

Especially preferably, each R^(5a) is independently

-   -   methyl or ethyl.

Each R⁶ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl or C₂-C₄-haloalkynyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁶ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl or        C₂-C₄-haloalkenyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

Especially preferably, each R⁶ is independently

-   -   H, methyl or ethyl.

Each R^(6a) preferably is independently

-   -   H, C₁-C₄-alkyl, C(O)R¹³ or C(O)OR¹³.

More preferably, each R^(6a) is independently

-   -   H or C₁-C₄-alkyl.

Especially preferably, each R^(6a) is independently

-   -   H, methyl or ethyl.

Each R⁷ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or        C₂-C₆-haloalkenyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁷ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₂-alkyl and C₁-C₂-haloalkyl.

Especially preferably, each R⁷ is independently

-   -   H, methyl, ethyl or trifluoromethyl.

Each R^(7a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(7a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(7a) is independently

-   -   methyl or ethyl.

Each R⁸ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁸ is independently

-   -   C₁-C₂-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R⁸ is independently

-   -   methyl or ethyl.

Each R^(8a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(8a) is independently

-   -   C₁-C₄-alkyl.

Especially preferably, each R^(8a) is independently

-   -   methyl or ethyl.

Each R⁹ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁹ is independently

-   -   C₁-C₂-alkyl, C₁-C₂-haloalkyl.

Especially preferably, each R⁹ is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R^(9a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(9a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(9a) is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R¹⁰ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl, C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹⁰ is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₃-C₇-cycloalkyl.

Especially preferably, each R¹⁰ is independently

-   -   H or methyl.

Each R¹¹ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹⁰ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl.

Especially preferably, each R¹¹ is independently

-   -   H, methyl or ethyl.

Each R^(11a) preferably is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₂-C₃-alkynyl.

More preferably, each R^(11a) is independently

-   -   H, C₁-C₄-alkyl, allyl or propargyl.

Especially preferably, each R^(11a) is independently

-   -   H, methyl or ethyl.

Each R¹² preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl.

More preferably, each R¹² is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹² is independently

-   -   H, methyl or ethyl.

Each R¹³ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl.

More preferably, each R¹³ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹³ is independently

-   -   methyl.

Each R¹⁴ preferably is independently

-   -   C₃-C₇-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) or        S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl, each substituted with 1 to 4 substituents        independently selected from the group consisting of cyano,        nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or        S(O)₂NR¹¹R¹²;    -   or phenyl, or a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄₋alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);

More preferably, each R¹⁴ is independently

-   -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Especially preferably, each R¹⁴ is independently

-   -   C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Each R¹⁵ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or phenyl optionally substituted with 1 to 5 substituents        independently selected from the group consisting of halogen,        cyano, OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,        S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, each R¹⁵ is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹⁵ is independently

-   -   methyl.

n preferably is 1, 2, 3 or 4. More preferably, n is 1, 2 or 3.Especially preferably, n is 1 or 2.

m preferably is 0, 1 or 2. More preferably, m is 0, 1 or 2. Especiallypreferably, m is 0 or 2.

X preferably is O or S. Especially preferably X is O.

Z preferably is O or S. Especially preferably Z is O.

In an individual embodiment, Q is U-1. In another individual embodiment,Q is U-2. In another individual embodiment, Q is U-3. In anotherindividual embodiment, Q is U-4. In another individual embodiment, Q isU-5. In another individual embodiment, Q is U-6. In another individualembodiment, Q is U-7. In another individual embodiment, Q is U-8. Inanother individual embodiment, Q is U-9. In another individualembodiment, Q is U-10. In another individual embodiment, Q is U-11. Inanother individual embodiment, Q is U-12. In another individualembodiment, Q is U-13. In another individual embodiment, Q is U-14. Inanother individual embodiment, Q is U-15. In another individualembodiment, Q is U-16. In another individual embodiment, Q is U-17. Inanother individual embodiment, Q is U-18. In another individualembodiment, Q is U-19. In another individual embodiment, Q is U-20. Inanother individual embodiment, Q is U-21. In another individualembodiment, Q is U-22. In another individual embodiment, Q is U-23. Inanother individual embodiment, Q is U-24. In another individualembodiment, Q is U-25. In another individual embodiment, Q is U-26. Inanother individual embodiment, Q is U-27. In another individualembodiment, Q is U-28. In another individual embodiment, Q is U-29. Inanother individual embodiment, Q is U-30. In another individualembodiment, Q is U-31. In another individual embodiment, Q is U-32. Inanother individual embodiment, Q is U-33. In another individualembodiment, Q is U-34. In another individual embodiment, Q is U-35. Inanother individual embodiment, Q is U-36. In another individualembodiment, Q is U-37. In another individual embodiment, Q is U-38. Inanother individual embodiment, Q is U-39. In another individualembodiment, Q is U-40. In another individual embodiment, Q is U-41. Inanother individual embodiment, Q is U-42. In another individualembodiment, Q is U-43. In another individual embodiment, Q is U-44. Inanother individual embodiment, Q is U-45. In another individualembodiment, Q is U-46. In another individual embodiment, Q is U-47. Inanother individual embodiment, Q is U-48. In another individualembodiment, Q is U-49. In another individual embodiment, Q is U-50. Inanother individual embodiment, Q is U-51. In another individualembodiment, Q is U-52. In another individual embodiment, Q is U-53. Inanother individual embodiment, Q is U-54. In another individualembodiment, Q is U-55. In another individual embodiment, Q is U-56. Inanother individual embodiment, Q is U-57. In another individualembodiment, Q is U-58. In another individual embodiment, Q is U-59. Inanother individual embodiment, Q is U-60. In another individualembodiment, Q is U-61. In another individual embodiment, Q is U-81. Inanother individual embodiment, Q is U-82. In another individualembodiment, Q is U-83. In another individual embodiment, Q is U-84. Inanother individual embodiment, Q is U-85. In another individualembodiment, Q is U-86. In another individual embodiment, Q is U-87. Inanother individual embodiment, Q is U-89. In another individualembodiment, Q is U-90. In another individual embodiment, Q is U-91. Inanother individual embodiment, Q is U-92. In another individualembodiment, Q is U-93. In another individual embodiment, Q is U-94. Inanother individual embodiment, Q is U-95. In another individualembodiment, Q is U-96. In another individual embodiment, Q is U-97. Inanother individual embodiment, Q is U-98. In another individualembodiment, Q is U-99. In another individual embodiment, Q is U-100. Inanother individual embodiment, Q is U-101. In another individualembodiment, Q is U-102. In another individual embodiment, Q is U-103. Inanother individual embodiment, Q is U-105. In another individualembodiment, Q is U-106. In another individual embodiment, Q is U-107. Inanother individual embodiment, Q is U-108. In another individualembodiment, Q is U-109. In another individual embodiment, Q is U-110. Inanother individual embodiment, Q is U-111. In another individualembodiment, Q is U-112. In another individual embodiment, Q is U-113. Inanother individual embodiment, Q is U-114. In another individualembodiment, Q is U-115. In another individual embodiment, Q is U-116. Inanother individual embodiment, Q is U-117. In another individualembodiment, Q is U-118. In another individual embodiment, Q is U-119. Inanother individual embodiment, Q is U-120. In another individualembodiment, Q is U-121. In another individual embodiment, Q is U-122. Inanother individual embodiment, Q is U-123.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), each R^(v) preferablyis independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹²;    -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹².

More preferably, each R^(v) is independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹².

Especially preferably, each R^(v) is independently

-   -   fluor, chlor, methoxy, trifluoromethyl, trifluoromethoxy or        methyl.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), r preferably is 0, 1,2, 3 or 4. More preferably, r is 0, 1, 2 or 3. Especially preferably, ris 1, 2 or 3.

A wide variety of synthetic methods are known in the art to enablepreparation of aromatic and nonaromatic heterocyclic rings and ringsystems; for extensive reviews see the eight volume set of ComprehensiveHeterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief,Pergamon Press, Oxford, 1984 and the twelve volume set of ComprehensiveHeterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V.Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. One skilled in the art will appreciate that onestereoisomer may be more active and/or may exhibit beneficial effectswhen enriched relative to the other stereoisomer(s) or when separatedfrom the other stereoisomer(s). Additionally, the skilled artisan knowshow to separate, enrich, and/or to selectively prepare saidstereoisomers. The compounds of the invention may be present as amixture of stereoisomers, individual stereoisomers or as an opticallyactive form.

Compounds selected from formula (I), (including all stereoisomers,N-oxides, and salts thereof), typically exist in more than one form, andformula (I) thus includes all crystalline and non-crystalline forms ofthe compounds that formula (I) represents. Non-crystalline forms includeembodiments which are solids such as waxes and gums as well asembodiments which are liquids such as solutions and melts. Crystallineforms include embodiments which represent essentially a single crystaltype and embodiments which represent a mixture of polymorphs (i.e.different crystalline types). The term “polymorph” refers to aparticular crystalline form of a chemical compound that can crystallizein different crystalline forms, these forms having differentarrangements and/or conformations of the molecules in the crystallattice. Although polymorphs can have the same chemical composition,they can also differ in composition due the presence or absence ofco-crystallized water or other molecules, which can be weakly orstrongly bound in the lattice. Polymorphs can differ in such chemical,physical and biological properties as crystal shape, density, hardness,color, chemical stability, melting point, hygroscopicity,suspensibility, dissolution rate and biological availability. Oneskilled in the art will appreciate that a polymorph of a compoundrepresented by formula (I) can exhibit beneficial effects (e.g.,suitability for preparation of useful formulations, improved biologicalperformance) relative to another polymorph or a mixture of polymorphs ofthe same compound represented by formula (I). Preparation and isolationof a particular polymorph of a compound represented by formula (I) canbe achieved by methods known to those skilled in the art including, forexample, crystallization using selected solvents and temperatures.

One skilled in the art will appreciate that not all nitrogen-containingheterocycles can form N-oxides since the nitrogen requires an availablelone pair for oxidation to the oxide; one skilled in the art willrecognize those nitrogen-containing heterocycles which can formN-oxides. One skilled in the art will also recognize that tertiaryamines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocycles and tertiary amines are very well known by oneskilled in the art including the oxidation of heterocycles and tertiaryamines with peroxy acids such as peracetic and 3-chloroperbenzoic acid(MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butylhydroperoxide, sodium perborate, and dioxiranes such asdimethyldioxirane. These methods for the preparation of N-oxides havebeen extensively described and reviewed in the literature, see forexample: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik inComprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keenein Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R.Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advancesin Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J.Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G.Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment andunder physiological conditions salts of chemical compounds are inequilibrium with their corresponding nonsalt forms, salts share thebiological utility of the nonsalt forms. Thus a wide variety of salts ofthe compounds of formula (I) are useful for control of parasiticnematodes. The salts of the compounds of formula (I) includeacid-addition salts with inorganic or organic acids such as hydrobromic,hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric,lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric,4-toluenesulfonic or valeric acids. When a compound of formula (I)contains an acidic moiety such as a carboxylic acid, phenol orsulfonylamide (i.e. when R³ is H), salts also include those formed withorganic or inorganic bases such as pyridine, triethylamine or ammonia,or amides, hydrides, hydroxides or carbonates of sodium, potassium,lithium, calcium, magnesium or barium. Accordingly, the presentinvention comprises compounds selected from formula (I), N-oxides andsalts thereof.

Embodiments of the present invention as described in the Summary of theInvention include those described below. In the following Embodiments,formula (I) includes stereoisomers, N-oxides, and salts thereof, andreference to “a compound of formula (I)” includes the definitions ofsubstituents specified in the Summary of the Invention unless furtherdefined in the embodiments.

EMBODIMENTS Embodiment 1

The compounds of the invention are defined in general terms by theformula (I). In a preferred embodiment, the compounds of the inventionare defined by formula (Ia):

whereinR¹, R², R³, R⁴, R^(4a), R⁵, R^(5a), R⁶, R^(6a), R⁷, R^(7a), R⁸, R^(8a),R⁹, R^(9a), R¹⁰, R¹¹, R^(11a), R¹², R¹³, R¹⁴, R¹⁵,Z, Q, R^(v), r, X, m and n are as defined above in the Summary of theInvention.

R¹ preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷,        N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹ or N(R¹⁰)S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, C(X)R⁷, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R¹ is

-   -   halogen, cyano, OR⁴, C₁-C₄-alkyl, C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;

Especially preferably, R¹ is

-   -   trifluoromethyl.

R² preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,        C₃-C₇-cycloalkyl, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R² is

-   -   H, halogen, cyano, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of cyano, OR⁴        and S(O)_(m)R⁹.

Especially preferably, R² is hydrogen.

R³ preferably is

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C(X)R⁷,        C(O)OR⁸ or C(O)NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, OR^(4a) and        S(O)_(m)R^(9a);    -   or C₁-C₄-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        C(X)R⁷ and C(O)OR⁸;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of phenyl or a        5- or 6-membered heteroaromatic ring, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴,        C₁-C₄-haloalkyl, C₂-C₆-alkoxyalkyl, C(X)R⁷, C(O)OR⁸, S(O)_(m)R⁹        and S(O)₂NR¹¹R¹².

More preferably, R³ is

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl, C(X)R⁷ or C(O)OR⁸;    -   or C₁-C₂-alkyl substituted with OR⁴;    -   or C₁-C₂-alkyl substituted with phenyl.

Especially preferably, R³ is hydrogen.

Q preferably is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₃-C₇-cycloalkyl, phenyl or a 5- or 6-membered heteroaromatic        ring system, each optionally substituted with 1 to 5        substituents independently selected from the group consisting of        halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹² and R¹⁴;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

More preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₇-cycloalkyl, phenyl or a 5-        or 6-membered heteroaromatic ring system, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹ and        S(O)₂NR¹¹R¹²;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

Even more preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₃-C₇-cycloalkyl;    -   or Q is selected from the group consisting of (U-1) to (U-61)        and (U-103).

Especially preferably, Q is methyl, ethyl or cyclopropyl or is selectedfrom the group consisting of (U-1), (U-49) and (U-103), particularly(U-1).

Each R⁴ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen.

More preferably, each R⁴ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R⁴ is independently methyl, ethyl, propyl,isopropyl, difluoromethyl or trifluoromethyl.

Each R^(4a) preferably is independently

-   -   H, C₁-C₆-alkyl or C₁-C₆-haloalkyl.

More preferably, each R^(4a) is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R^(4a) is independently

-   -   methyl or ethyl.

Each R⁵ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl;        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁵ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹².

Especially preferably, each R⁵ is independently

-   -   H, methyl or ethyl.

Each R^(5a) preferably is independently

-   -   H or C₁-C₄-alkyl.

More preferably, each R^(5a) is independently

-   -   H or C₁-C₂-alkyl.

Especially preferably, each R^(5a) is independently

-   -   methyl or ethyl.

Each R⁶ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl or C₂-C₄-haloalkynyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁶ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl or        C₂-C₄-haloalkenyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

Especially preferably, each R⁶ is independently

-   -   H, methyl or ethyl.

Each R^(6a) preferably is independently

-   -   H, C₁-C₄-alkyl, C(O)R¹³ or C(O)OR¹³.

More preferably, each R^(6a) is independently

-   -   H or C₁-C₄-alkyl.

Especially preferably, each R^(6a) is independently

-   -   H, methyl or ethyl.

Each R⁷ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or        C₂-C₆-haloalkenyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁷ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₂-alkyl and C₁-C₂-haloalkyl.

Especially preferably, each R⁷ is independently

-   -   H, methyl, ethyl or trifluoromethyl.

Each R^(7a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(7a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(7a) is independently

-   -   methyl or ethyl.

Each R⁸ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁸ is independently

-   -   C₁-C₂-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R⁸ is independently

-   -   methyl or ethyl.

Each R^(8a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(8a) is independently

-   -   C₁-C₄-alkyl.

Especially preferably, each R^(8a) is independently

-   -   methyl or ethyl.

Each R⁹ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁹ is independently

-   -   C₁-C₂-alkyl, C₁-C₂-haloalkyl.

Especially preferably, each R⁹ is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R^(9a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(9a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(9a) is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R¹⁰ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl, C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹⁰ is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₃-C₇-cycloalkyl.

Especially preferably, each R¹⁰ is independently

-   -   H or methyl.

Each R¹¹ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹¹ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl.

Especially preferably, each R¹¹ is independently

-   -   H, methyl or ethyl.

Each R^(11a) preferably is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₂-C₃-alkynyl.

More preferably, each R^(11a) is independently

-   -   H, C₁-C₄-alkyl, allyl or propargyl.

Especially preferably, each R^(11a) is independently

-   -   H, methyl or ethyl.

Each R¹² preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl.

More preferably, each R¹² is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹² is independently

-   -   H, methyl or ethyl.

Each R¹³ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl.

More preferably, each R¹³ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹³ is independently

-   -   methyl.

Each R¹⁴ preferably is independently

-   -   C₃-C₇-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) or        S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl, each substituted with 1 to 4 substituents        independently selected from the group consisting of cyano,        nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or        S(O)₂NR¹¹R¹²;    -   or phenyl, or a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);

More preferably, each R¹⁴ is independently

-   -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Especially preferably, each R¹⁴ is independently

-   -   C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Each R¹⁵ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or phenyl optionally substituted with 1 to 5 substituents        independently selected from the group consisting of halogen,        cyano, OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,        S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, each R¹⁵ is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹⁵ is independently

-   -   methyl.

n preferably is 1, 2, 3 or 4. More preferably, n is 1, 2 or 3.Especially preferably, n is 1 or 2.

m preferably is 0, 1 or 2. More preferably, m is 0, 1 or 2. Especiallypreferably, m is 0 or 2.

X preferably is O or S. Especially preferably X is O.

Z preferably is O or S. Especially preferably Z is O.

In an individual type of this embodiment, Q is U-1. In anotherindividual type of this embodiment, Q is U-2. In another individual typeof this embodiment, Q is U-3. In another individual type of thisembodiment, Q is U-4. In another individual type of this embodiment, Qis U-5. In another individual type of this embodiment, Q is U-6. Inanother individual type of this embodiment, Q is U-7. In anotherindividual type of this embodiment, Q is U-8. In another individual typeof this embodiment, Q is U-9. In another individual type of thisembodiment, Q is U-10. In another individual type of this embodiment, Qis U-11. In another individual type of this embodiment, Q is U-12. Inanother individual type of this embodiment, Q is U-13. In anotherindividual type of this embodiment, Q is U-14. In another individualtype of this embodiment, Q is U-15. In another individual type of thisembodiment, Q is U-16. In another individual type of this embodiment, Qis U-17. In another individual type of this embodiment, Q is U-18. Inanother individual type of this embodiment, Q is U-19. In anotherindividual type of this embodiment, Q is U-20. In another individualtype of this embodiment, Q is U-21. In another individual type of thisembodiment, Q is U-22. In another individual type of this embodiment, Qis U-23. In another individual type of this embodiment, Q is U-24. Inanother individual type of this embodiment, Q is U-25. In anotherindividual type of this embodiment, Q is U-26. In another individualtype of this embodiment, Q is U-27. In another individual type of thisembodiment, Q is U-28. In another individual type of this embodiment, Qis U-29. In another individual type of this embodiment, Q is U-30. Inanother individual type of this embodiment, Q is U-31. In anotherindividual type of this embodiment, Q is U-32. In another individualtype of this embodiment, Q is U-33. In another individual type of thisembodiment, Q is U-34. In another individual type of this embodiment, Qis U-35. In another individual type of this embodiment, Q is U-36. Inanother individual type of this embodiment, Q is U-37. In anotherindividual type of this embodiment, Q is U-38. In another individualtype of this embodiment, Q is U-39. In another individual type of thisembodiment, Q is U-40. In another individual type of this embodiment, Qis U-41. In another individual type of this embodiment, Q is U-42. Inanother individual type of this embodiment, Q is U-43. In anotherindividual type of this embodiment, Q is U-44. In another individualtype of this embodiment, Q is U-45. In another individual type of thisembodiment, Q is U-46. In another individual type of this embodiment, Qis U-47. In another individual type of this embodiment, Q is U-48. Inanother individual type of this embodiment, Q is U-49. In anotherindividual type of this embodiment, Q is U-50. In another individualtype of this embodiment, Q is U-51. In another individual type of thisembodiment, Q is U-52. In another individual type of this embodiment, Qis U-53. In another individual type of this embodiment, Q is U-54. Inanother individual type of this embodiment, Q is U-55. In anotherindividual type of this embodiment, Q is U-56. In another individualtype of this embodiment, Q is U-57. In another individual type of thisembodiment, Q is U-58. In another individual type of this embodiment, Qis U-59. In another individual type of this embodiment, Q is U-60. Inanother individual type of this embodiment, Q is U-61. In anotherindividual type of this embodiment, Q is U-81. In another individualtype of this embodiment, Q is U-82. In another individual type of thisembodiment, Q is U-83. In another individual type of this embodiment, Qis U-84. In another individual type of this embodiment, Q is U-85. Inanother individual type of this embodiment, Q is U-86. In anotherindividual type of this embodiment, Q is U-87. In another individualtype of this embodiment, Q is U-89. In another individual type of thisembodiment, Q is U-90. In another individual type of this embodiment, Qis U-91. In another individual type of this embodiment, Q is U-92. Inanother individual type of this embodiment, Q is U-93. In anotherindividual type of this embodiment, Q is U-94. In another individualtype of this embodiment, Q is U-95. In another individual type of thisembodiment, Q is U-96. In another individual type of this embodiment, Qis U-97. In another individual type of this embodiment, Q is U-98. Inanother individual type of this embodiment, Q is U-99. In anotherindividual type of this embodiment, Q is U-100. In another individualtype of this embodiment, Q is U-101. In another individual type of thisembodiment, Q is U-102. In another individual type of this embodiment, Qis U-103. In another individual type of this embodiment, Q is U-105. Inanother individual type of this embodiment, Q is U-106. In anotherindividual type of this embodiment, Q is U-107. In another individualtype of this embodiment, Q is U-108. In another individual type of thisembodiment, Q is U-109. In another individual type of this embodiment, Qis U-110. In another individual type of this embodiment, Q is U-111. Inanother individual type of this embodiment, Q is U-112. In anotherindividual type of this embodiment, Q is U-113. In another individualtype of this embodiment, Q is U-114. In another individual type of thisembodiment, Q is U-115. In another individual type of this embodiment, Qis U-116. In another individual type of this embodiment, Q is U-117. Inanother individual type of this embodiment, Q is U-118. In anotherindividual type of this embodiment, Q is U-119. In another individualtype of this embodiment, Q is U-120. In another individual type of thisembodiment, Q is U-121. In another individual type of this embodiment, Qis U-122. In another individual type of this embodiment, Q is U-123.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), each R^(v) preferablyis independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹²;    -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹².

More preferably, each R^(v) is independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹².

Especially preferably, each R^(v) is independently

-   -   fluor, chlor, methoxy, trifluoromethyl, trifluoromethoxy or        methyl.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), r preferably is 0, 1,2, 3 or 4. More preferably, r is 0, 1, 2 or 3. Especially preferably, ris 1, 2 or 3.

A specific aspect of the compounds of this embodiment are compoundswhich are represented by formula (Ia-1)

wherein the structural elements are defined as given above forembodiment 1.

Embodiment 2

The compounds of the invention are defined in general terms by theformula (I). In another preferred embodiment, the compounds of theinvention are defined by formula (Ib):

whereinR¹, R², R³, R⁴, R^(4a), R⁵, R^(5a), R⁶, R^(6a), R⁷, R^(7a), R⁸, R^(8a),R⁹, R^(9a), R¹⁰, R¹¹, R^(11a), R¹², R¹³, R¹⁴, R¹⁵, Z, Q, R^(v), r, X, mand n are as defined above in the Summary of the Invention.

R¹ preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷,        N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹ or N(R¹⁰)S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, C(X)R⁷, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R¹ is

-   -   halogen, cyano, OR⁴, C₁-C₄-alkyl, C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;

Especially preferably, R¹ is

-   -   chlorine or trifluoromethyl.

R² preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,        C₃-C₇-cycloalkyl, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R² is

-   -   H, halogen, cyano, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of cyano, OR⁴        and S(O)_(m)R⁹.

Especially preferably, R² is hydrogen.

R³ preferably is

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C(X)R⁷,        C(O)OR⁸ or C(O)NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, OR^(4a) and        S(O)_(m)R^(9a);    -   or C₁-C₄-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        C(X)R⁷ and C(O)OR⁸;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of phenyl or a        5- or 6-membered heteroaromatic ring, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴,        C₁-C₄-haloalkyl, C₂-C₆-alkoxyalkyl, C(X)R⁷, C(O)OR⁸, S(O)_(m)R⁹        and S(O)₂NR¹¹R¹².

More preferably, R³ is

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl, C(X)R⁷ or C(O)OR⁸;    -   or C₁-C₂-alkyl substituted with OR⁴;    -   or C₁-C₂-alkyl substituted with phenyl.

Especially preferably, R³ is hydrogen.

Q preferably is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₃-C₇-cycloalkyl, phenyl or a 5- or 6-membered heteroaromatic        ring system, each optionally substituted with 1 to 5        substituents independently selected from the group consisting of        halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹² and R¹⁴;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

More preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₇-cycloalkyl, phenyl or a 5-        or 6-membered heteroaromatic ring system, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹ and        S(O)₂NR¹¹R¹²;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

Even more preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₃-C₇-cycloalkyl;    -   or Q is selected from the group consisting of (U-1) to (U-61)        and (U-103).

Especially preferably, Q is methyl, ethyl or cyclopropyl or is selectedfrom the group consisting of (U-1), (U-49) and (U-103), particularly(U-1).

Each R⁴ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen.

More preferably, each R⁴ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R⁴ is independently methyl, ethyl, propyl,isopropyl, difluoromethyl or trifluoromethyl.

Each R^(4a) preferably is independently

-   -   H, C₁-C₆-alkyl or C₁-C₆-haloalkyl.

More preferably, each R^(4a) is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R^(4a) is independently

-   -   methyl or ethyl.

Each R⁵ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl;        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁵ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹².

Especially preferably, each R⁵ is independently

-   -   H, methyl or ethyl.

Each R^(5a) preferably is independently

-   -   H or C₁-C₄-alkyl.

More preferably, each R^(5a) is independently

-   -   H or C₁-C₂-alkyl.

Especially preferably, each R^(5a) is independently

-   -   methyl or ethyl.

Each R⁶ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl or C₂-C₄-haloalkynyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁶ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl or        C₂-C₄-haloalkenyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

Especially preferably, each R⁶ is independently

-   -   H, methyl or ethyl.

Each R^(6a) preferably is independently

-   -   H, C₁-C₄-alkyl, C(O)R¹³ or C(O)OR¹³.

More preferably, each R^(6a) is independently

-   -   H or C₁-C₄-alkyl.

Especially preferably, each R^(6a) is independently

-   -   H, methyl or ethyl.

Each R⁷ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or        C₂-C₆-haloalkenyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁷ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₂-alkyl and C₁-C₂-haloalkyl.

Especially preferably, each R⁷ is independently

-   -   H, methyl, ethyl or trifluoromethyl.

Each R^(7a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(7a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(7a) is independently

-   -   methyl or ethyl.

Each R⁸ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁸ is independently

-   -   C₁-C₂-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R⁸ is independently

-   -   methyl or ethyl.

Each R^(8a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(8a) is independently

-   -   C₁-C₄-alkyl.

Especially preferably, each R^(8a) is independently

-   -   methyl or ethyl.

Each R⁹ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁹ is independently

-   -   C₁-C₂-alkyl, C₁-C₂-haloalkyl.

Especially preferably, each R⁹ is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R^(9a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(9a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(9a) is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R¹⁰ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl, C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹⁰ is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₃-C₇-cycloalkyl.

Especially preferably, each R¹⁰ is independently

-   -   H or methyl.

Each R¹¹ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹¹ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl.

Especially preferably, each R¹¹ is independently

-   -   H, methyl or ethyl.

Each R^(11a) preferably is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₂-C₃-alkynyl.

More preferably, each R^(11a) is independently

-   -   H, C₁-C₄-alkyl, allyl or propargyl.

Especially preferably, each R^(11a) is independently

-   -   H, methyl or ethyl.

Each R¹² preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl.

More preferably, each R¹² is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹² is independently

-   -   H, methyl or ethyl.

Each R¹³ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl.

More preferably, each R¹³ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹³ is independently

-   -   methyl.

Each R¹⁴ preferably is independently

-   -   C₃-C₇-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) or        S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl, each substituted with 1 to 4 substituents        independently selected from the group consisting of cyano,        nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or        S(O)₂NR¹¹R¹²;    -   or phenyl, or a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄₋alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);

More preferably, each R¹⁴ is independently

-   -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Especially preferably, each R¹⁴ is independently

-   -   C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Each R¹⁵ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or phenyl optionally substituted with 1 to 5 substituents        independently selected from the group consisting of halogen,        cyano, OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,        S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, each R¹⁵ is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹⁵ is independently

-   -   methyl.

n preferably is 1, 2, 3 or 4. More preferably, n is 1, 2 or 3.Especially preferably, n is 1 or 2.

m preferably is 0, 1 or 2. More preferably, m is 0, 1 or 2. Especiallypreferably, m is 0 or 2.

X preferably is O or S. Especially preferably X is O.

Z preferably is O or S. Especially preferably Z is O.

In an individual type of this embodiment, Q is U-1. In anotherindividual type of this embodiment, Q is U-2. In another individual typeof this embodiment, Q is U-3. In another individual type of thisembodiment, Q is U-4. In another individual type of this embodiment, Qis U-5. In another individual type of this embodiment, Q is U-6. Inanother individual type of this embodiment, Q is U-7. In anotherindividual type of this embodiment, Q is U-8. In another individual typeof this embodiment, Q is U-9. In another individual type of thisembodiment, Q is U-10. In another individual type of this embodiment, Qis U-11. In another individual type of this embodiment, Q is U-12. Inanother individual type of this embodiment, Q is U-13. In anotherindividual type of this embodiment, Q is U-14. In another individualtype of this embodiment, Q is U-15. In another individual type of thisembodiment, Q is U-16. In another individual type of this embodiment, Qis U-17. In another individual type of this embodiment, Q is U-18. Inanother individual type of this embodiment, Q is U-19. In anotherindividual type of this embodiment, Q is U-20. In another individualtype of this embodiment, Q is U-21. In another individual type of thisembodiment, Q is U-22. In another individual type of this embodiment, Qis U-23. In another individual type of this embodiment, Q is U-24. Inanother individual type of this embodiment, Q is U-25. In anotherindividual type of this embodiment, Q is U-26. In another individualtype of this embodiment, Q is U-27. In another individual type of thisembodiment, Q is U-28. In another individual type of this embodiment, Qis U-29. In another individual type of this embodiment, Q is U-30. Inanother individual type of this embodiment, Q is U-31. In anotherindividual type of this embodiment, Q is U-32. In another individualtype of this embodiment, Q is U-33. In another individual type of thisembodiment, Q is U-34. In another individual type of this embodiment, Qis U-35. In another individual type of this embodiment, Q is U-36. Inanother individual type of this embodiment, Q is U-37. In anotherindividual type of this embodiment, Q is U-38. In another individualtype of this embodiment, Q is U-39. In another individual type of thisembodiment, Q is U-40. In another individual type of this embodiment, Qis U-41. In another individual type of this embodiment, Q is U-42. Inanother individual type of this embodiment, Q is U-43. In anotherindividual type of this embodiment, Q is U-44. In another individualtype of this embodiment, Q is U-45. In another individual type of thisembodiment, Q is U-46. In another individual type of this embodiment, Qis U-47. In another individual type of this embodiment, Q is U-48. Inanother individual type of this embodiment, Q is U-49. In anotherindividual type of this embodiment, Q is U-50. In another individualtype of this embodiment, Q is U-51. In another individual type of thisembodiment, Q is U-52. In another individual type of this embodiment, Qis U-53. In another individual type of this embodiment, Q is U-54. Inanother individual type of this embodiment, Q is U-55. In anotherindividual type of this embodiment, Q is U-56. In another individualtype of this embodiment, Q is U-57. In another individual type of thisembodiment, Q is U-58. In another individual type of this embodiment, Qis U-59. In another individual type of this embodiment, Q is U-60. Inanother individual type of this embodiment, Q is U-61. In anotherindividual type of this embodiment, Q is U-81. In another individualtype of this embodiment, Q is U-82. In another individual type of thisembodiment, Q is U-83. In another individual type of this embodiment, Qis U-84. In another individual type of this embodiment, Q is U-85. Inanother individual type of this embodiment, Q is U-86. In anotherindividual type of this embodiment, Q is U-87. In another individualtype of this embodiment, Q is U-89. In another individual type of thisembodiment, Q is U-90. In another individual type of this embodiment, Qis U-91. In another individual type of this embodiment, Q is U-92. Inanother individual type of this embodiment, Q is U-93. In anotherindividual type of this embodiment, Q is U-94. In another individualtype of this embodiment, Q is U-95. In another individual type of thisembodiment, Q is U-96. In another individual type of this embodiment, Qis U-97. In another individual type of this embodiment, Q is U-98. Inanother individual type of this embodiment, Q is U-99. In anotherindividual type of this embodiment, Q is U-100. In another individualtype of this embodiment, Q is U-101. In another individual type of thisembodiment, Q is U-102. In another individual type of this embodiment, Qis U-103. In another individual type of this embodiment, Q is U-105. Inanother individual type of this embodiment, Q is U-106. In anotherindividual type of this embodiment, Q is U-107. In another individualtype of this embodiment, Q is U-108. In another individual type of thisembodiment, Q is U-109. In another individual type of this embodiment, Qis U-110. In another individual type of this embodiment, Q is U-111. Inanother individual type of this embodiment, Q is U-112. In anotherindividual type of this embodiment, Q is U-113. In another individualtype of this embodiment, Q is U-114. In another individual type of thisembodiment, Q is U-115. In another individual type of this embodiment, Qis U-116. In another individual type of this embodiment, Q is U-117. Inanother individual type of this embodiment, Q is U-118. In anotherindividual type of this embodiment, Q is U-119. In another individualtype of this embodiment, Q is U-120. In another individual type of thisembodiment, Q is U-121. In another individual type of this embodiment, Qis U-122. In another individual type of this embodiment, Q is U-123.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), each R^(v) preferablyis independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹²;    -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹².

More preferably, each R^(v) is independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹².

Especially preferably, each R^(v) is independently

-   -   fluor, chlor, methoxy, trifluoromethyl, trifluoromethoxy or        methyl.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), r preferably is 0, 1,2, 3 or 4. More preferably, r is 0, 1, 2 or 3. Especially preferably, ris 1, 2 or 3.

A specific aspect of the compounds of this embodiment are compoundswhich are represented by formula (Ib-1)

wherein the structural elements are defined as given above forembodiment 2.

Embodiment 3

The compounds of the invention are defined in general terms by theformula (I). In another preferred embodiment, the compounds of theinvention are defined by formula (Ic):

whereinR¹, R², R³, R⁴, R^(4a), R⁵, R^(5a), R⁶, R^(6a), R⁷, R^(7a), R⁸, R^(8a),R⁹, R^(9a), R¹⁰, R¹¹, R^(11a), R¹², R¹³, R¹⁴, R¹⁵, Z, Q, R^(v), r, X, mand n are as defined above in the Summary of the Invention.

R¹ preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷,        N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹ or N(R¹⁰)S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, C(X)R⁷, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R¹ is

-   -   halogen, cyano, OR⁴, C₁-C₄-alkyl, C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;

Especially preferably, R¹ is

-   -   trifluoromethyl.

R² preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,        C₃-C₇-cycloalkyl, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R² is

-   -   H, halogen, cyano, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of cyano, OR⁴        and S(O)_(m)R⁹.

Especially preferably, R² is hydrogen.

R³ preferably is

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C(X)R⁷,        C(O)OR⁸ or C(O)NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, OR^(4a) and        S(O)_(m)R^(9a);    -   or C₁-C₄-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        C(X)R⁷ and C(O)OR⁸;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of phenyl or a        5- or 6-membered heteroaromatic ring, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴,        C₁-C₄-haloalkyl, C₂-C₆-alkoxyalkyl, C(X)R⁷, C(O)OR⁸, S(O)_(m)R⁹        and S(O)₂NR¹¹R¹².

More preferably, R³ is

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl, C(X)R⁷ or C(O)OR⁸;    -   or C₁-C₂-alkyl substituted with OR⁴;    -   or C₁-C₂-alkyl substituted with phenyl.

Especially preferably, R³ is hydrogen.

Q preferably is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₃-C₇-cycloalkyl, phenyl or a 5- or 6-membered heteroaromatic        ring system, each optionally substituted with 1 to 5        substituents independently selected from the group consisting of        halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹² and R¹⁴;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

More preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₇-cycloalkyl, phenyl or a 5-        or 6-membered heteroaromatic ring system, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹ and        S(O)₂NR¹¹R¹²;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

Even more preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₃-C₇-cycloalkyl;    -   or Q is selected from the group consisting of (U-1) to (U-61)        and (U-103).

Especially preferably, Q is methyl, ethyl or cyclopropyl or is selectedfrom the group consisting of (U-1), (U-49) and (U-103), particularly(U-1).

Each R⁴ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen.

More preferably, each R⁴ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R⁴ is independently methyl, ethyl, propyl,isopropyl, difluoromethyl or trifluoromethyl.

Each R^(4a) preferably is independently

-   -   H, C₁-C₆-alkyl or C₁-C₆-haloalkyl.

More preferably, each R^(4a) is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R^(4a) is independently

-   -   methyl or ethyl.

Each R⁵ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl;        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁵ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹².

Especially preferably, each R⁵ is independently

-   -   H, methyl or ethyl.

Each R^(5a) preferably is independently

-   -   H or C₁-C₄-alkyl.

More preferably, each R^(5a) is independently

-   -   H or C₁-C₂-alkyl.

Especially preferably, each R^(5a) is independently

-   -   methyl or ethyl.

Each R⁶ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl or C₂-C₄-haloalkynyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁶ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl or        C₂-C₄-haloalkenyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

Especially preferably, each R⁶ is independently

-   -   H, methyl or ethyl.

Each R^(6a) preferably is independently

-   -   H, C₁-C₄-alkyl, C(O)R¹³ or C(O)OR¹³.

More preferably, each R^(6a) is independently

-   -   H or C₁-C₄-alkyl.

Especially preferably, each R^(6a) is independently

-   -   H, methyl or ethyl.

Each R⁷ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or        C₂-C₆-haloalkenyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁷ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₂-alkyl and C₁-C₂-haloalkyl.

Especially preferably, each R⁷ is independently

-   -   H, methyl, ethyl or trifluoromethyl.

Each R^(7a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(7a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(7a) is independently

-   -   methyl or ethyl.

Each R⁸ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁸ is independently

-   -   C₁-C₂-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R⁸ is independently

-   -   methyl or ethyl.

Each R^(8a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(8a) is independently

-   -   C₁-C₄-alkyl.

Especially preferably, each R^(8a) is independently

-   -   methyl or ethyl.

Each R⁹ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁹ is independently

-   -   C₁-C₂-alkyl, C₁-C₂-haloalkyl.

Especially preferably, each R⁹ is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R^(9a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(9a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(9a) is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R¹⁰ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl, C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹⁰ is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₃-C₇-cycloalkyl.

Especially preferably, each R¹⁰ is independently

-   -   H or methyl.

Each R¹¹ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹¹ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl.

Especially preferably, each R¹¹ is independently

-   -   H, methyl or ethyl.

Each R^(11a) preferably is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₂-C₃-alkynyl.

More preferably, each R^(11a) is independently

-   -   H, C₁-C₄-alkyl, allyl or propargyl.

Especially preferably, each R^(11a) is independently

-   -   H, methyl or ethyl.

Each R¹² preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂—C haloalkynyl.

More preferably, each R¹² is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹² is independently

-   -   H, methyl or ethyl.

Each R¹³ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂—C haloalkynyl.

More preferably, each R¹³ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹³ is independently

-   -   methyl.

Each R¹⁴ preferably is independently

-   -   C₃-C₇-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) or        S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl, each substituted with 1 to 4 substituents        independently selected from the group consisting of cyano,        nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or        S(O)₂NR¹¹R¹²;    -   or phenyl, or a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄₋alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);

More preferably, each R¹⁴ is independently

-   -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Especially preferably, each R¹⁴ is independently

-   -   C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Each R¹⁵ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or phenyl optionally substituted with 1 to 5 substituents        independently selected from the group consisting of halogen,        cyano, OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,        S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, each R¹⁵ is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹⁵ is independently

-   -   methyl.

n preferably is 1, 2, 3 or 4. More preferably, n is 1, 2 or 3.Especially preferably, n is 1 or 2.

m preferably is 0, 1 or 2. More preferably, m is 0, 1 or 2. Especiallypreferably, m is 0 or 2.

X preferably is O or S. Especially preferably X is O.

Z preferably is O or S. Especially preferably Z is O.

In an individual type of this embodiment, Q is U-1. In anotherindividual type of this embodiment, Q is U-2. In another individual typeof this embodiment, Q is U-3. In another individual type of thisembodiment, Q is U-4. In another individual type of this embodiment, Qis U-5. In another individual type of this embodiment, Q is U-6. Inanother individual type of this embodiment, Q is U-7. In anotherindividual type of this embodiment, Q is U-8. In another individual typeof this embodiment, Q is U-9. In another individual type of thisembodiment, Q is U-10. In another individual type of this embodiment, Qis U-11. In another individual type of this embodiment, Q is U-12. Inanother individual type of this embodiment, Q is U-13. In anotherindividual type of this embodiment, Q is U-14. In another individualtype of this embodiment, Q is U-15. In another individual type of thisembodiment, Q is U-16. In another individual type of this embodiment, Qis U-17. In another individual type of this embodiment, Q is U-18. Inanother individual type of this embodiment, Q is U-19. In anotherindividual type of this embodiment, Q is U-20. In another individualtype of this embodiment, Q is U-21. In another individual type of thisembodiment, Q is U-22. In another individual type of this embodiment, Qis U-23. In another individual type of this embodiment, Q is U-24. Inanother individual type of this embodiment, Q is U-25. In anotherindividual type of this embodiment, Q is U-26. In another individualtype of this embodiment, Q is U-27. In another individual type of thisembodiment, Q is U-28. In another individual type of this embodiment, Qis U-29. In another individual type of this embodiment, Q is U-30. Inanother individual type of this embodiment, Q is U-31. In anotherindividual type of this embodiment, Q is U-32. In another individualtype of this embodiment, Q is U-33. In another individual type of thisembodiment, Q is U-34. In another individual type of this embodiment, Qis U-35. In another individual type of this embodiment, Q is U-36. Inanother individual type of this embodiment, Q is U-37. In anotherindividual type of this embodiment, Q is U-38. In another individualtype of this embodiment, Q is U-39. In another individual type of thisembodiment, Q is U-40. In another individual type of this embodiment, Qis U-41. In another individual type of this embodiment, Q is U-42. Inanother individual type of this embodiment, Q is U-43. In anotherindividual type of this embodiment, Q is U-44. In another individualtype of this embodiment, Q is U-45. In another individual type of thisembodiment, Q is U-46. In another individual type of this embodiment, Qis U-47. In another individual type of this embodiment, Q is U-48. Inanother individual type of this embodiment, Q is U-49. In anotherindividual type of this embodiment, Q is U-50. In another individualtype of this embodiment, Q is U-51. In another individual type of thisembodiment, Q is U-52. In another individual type of this embodiment, Qis U-53. In another individual type of this embodiment, Q is U-54. Inanother individual type of this embodiment, Q is U-55. In anotherindividual type of this embodiment, Q is U-56. In another individualtype of this embodiment, Q is U-57. In another individual type of thisembodiment, Q is U-58. In another individual type of this embodiment, Qis U-59. In another individual type of this embodiment, Q is U-60. Inanother individual type of this embodiment, Q is U-61. In anotherindividual type of this embodiment, Q is U-81. In another individualtype of this embodiment, Q is U-82. In another individual type of thisembodiment, Q is U-83. In another individual type of this embodiment, Qis U-84. In another individual type of this embodiment, Q is U-85. Inanother individual type of this embodiment, Q is U-86. In anotherindividual type of this embodiment, Q is U-87. In another individualtype of this embodiment, Q is U-89. In another individual type of thisembodiment, Q is U-90. In another individual type of this embodiment, Qis U-91. In another individual type of this embodiment, Q is U-92. Inanother individual type of this embodiment, Q is U-93. In anotherindividual type of this embodiment, Q is U-94. In another individualtype of this embodiment, Q is U-95. In another individual type of thisembodiment, Q is U-96. In another individual type of this embodiment, Qis U-97. In another individual type of this embodiment, Q is U-98. Inanother individual type of this embodiment, Q is U-99. In anotherindividual type of this embodiment, Q is U-100. In another individualtype of this embodiment, Q is U-101. In another individual type of thisembodiment, Q is U-102. In another individual type of this embodiment, Qis U-103. In another individual type of this embodiment, Q is U-105. Inanother individual type of this embodiment, Q is U-106. In anotherindividual type of this embodiment, Q is U-107. In another individualtype of this embodiment, Q is U-108. In another individual type of thisembodiment, Q is U-109. In another individual type of this embodiment, Qis U-110. In another individual type of this embodiment, Q is U-111. Inanother individual type of this embodiment, Q is U-112. In anotherindividual type of this embodiment, Q is U-113. In another individualtype of this embodiment, Q is U-114. In another individual type of thisembodiment, Q is U-115. In another individual type of this embodiment, Qis U-116. In another individual type of this embodiment, Q is U-117. Inanother individual type of this embodiment, Q is U-118. In anotherindividual type of this embodiment, Q is U-119. In another individualtype of this embodiment, Q is U-120. In another individual type of thisembodiment, Q is U-121. In another individual type of this embodiment, Qis U-122. In another individual type of this embodiment, Q is U-123.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), each R^(v) preferablyis independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹²;    -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹².

More preferably, each R^(v) is independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹².

Especially preferably, each R^(v) is independently

-   -   fluor, chlor, methoxy, trifluoromethyl, trifluoromethoxy or        methyl.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), r preferably is 0, 1,2, 3 or 4. More preferably, r is 0, 1, 2 or 3. Especially preferably, ris 1, 2 or 3.

Embodiment 4

The compounds of the invention are defined in general terms by theformula (I). In a preferred embodiment, the compounds of the inventionare defined by formula (Id):

wherein

R¹, R², R³, R⁴, R^(4a), R⁵, R^(5a), R⁶, R^(6a), R⁷, R^(7a), R⁸, R^(8a),R⁹, R^(9a), R¹⁰, R¹¹, R^(11a), R¹², R¹³, R¹⁴, R¹⁵, Z, Q, R^(v), r, X, mand n are as defined above in the Summary of the Invention.

R¹ preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷,        N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹ or N(R¹⁰)S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, C(X)R⁷, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R¹ is

-   -   halogen, cyano, OR⁴, C₁-C₄-alkyl, C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;

Especially preferably, R¹ is

-   -   trifluoromethyl.

R² preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,        C₃-C₇-cycloalkyl, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R² is

-   -   H, halogen, cyano, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of cyano, OR⁴        and S(O)_(m)R⁹.

Especially preferably, R² is hydrogen.

R³ preferably is

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C(X)R⁷,        C(O)OR⁸ or C(O)NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, OR^(4a) and        S(O)_(m)R^(9a);    -   or C₁-C₄-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        C(X)R⁷ and C(O)OR⁸;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of phenyl or a        5- or 6-membered heteroaromatic ring, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴,        C₁-C₄-haloalkyl, C₂-C₆-alkoxyalkyl, C(X)R⁷, C(O)OR⁸, S(O)_(m)R⁹        and S(O)₂NR¹¹R¹².

More preferably, R³ is

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl, C(X)R⁷ or C(O)OR⁸;    -   or C₁-C₂-alkyl substituted with OR⁴;    -   or C₁-C₂-alkyl substituted with phenyl.

Especially preferably, R³ is hydrogen.

Q preferably is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₃-C₇-cycloalkyl, phenyl or a 5- or 6-membered heteroaromatic        ring system, each optionally substituted with 1 to 5        substituents independently selected from the group consisting of        halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹² and R¹⁴;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

More preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₇-cycloalkyl, phenyl or a 5-        or 6-membered heteroaromatic ring system, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹ and        S(O)₂NR¹¹R¹²;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

Even more preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₃-C₇-cycloalkyl;    -   or Q is selected from the group consisting of (U-1) to (U-61)        and (U-103).

Especially preferably, Q is methyl, ethyl or cyclopropyl or is selectedfrom the group consisting of (U-1), (U-49) and (U-103), particularly(U-1).

Each R⁴ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen.

More preferably, each R⁴ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R⁴ is independently methyl, ethyl, propyl,isopropyl, difluoromethyl or trifluoromethyl.

Each R^(4a) preferably is independently

-   -   H, C₁-C₆-alkyl or C₁-C₆-haloalkyl.

More preferably, each R^(4a) is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R^(4a) is independently

-   -   methyl or ethyl.

Each R⁵ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl;        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁵ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹².

Especially preferably, each R⁵ is independently

-   -   H, methyl or ethyl.

Each R^(5a) preferably is independently

-   -   H or C₁-C₄-alkyl.

More preferably, each R^(5a) is independently

-   -   H or C₁-C₂-alkyl.

Especially preferably, each R^(5a) is independently

-   -   methyl or ethyl.

Each R⁶ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl or C₂-C₄-haloalkynyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁶ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl or        C₂-C₄-haloalkenyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

Especially preferably, each R⁶ is independently

-   -   H, methyl or ethyl.

Each R^(6a) preferably is independently

-   -   H, C₁-C₄-alkyl, C(O)R¹³ or C(O)OR¹³.

More preferably, each R^(6a) is independently

-   -   H or C₁-C₄-alkyl.

Especially preferably, each R^(6a) is independently

-   -   H, methyl or ethyl.

Each R⁷ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or        C₂-C₆-haloalkenyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁷ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₂-alkyl and C₁-C₂-haloalkyl.

Especially preferably, each R⁷ is independently

-   -   H, methyl, ethyl or trifluoromethyl.

Each R^(7a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(7a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(7a) is independently

-   -   methyl or ethyl.

Each R⁸ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁸ is independently

-   -   C₁-C₂-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R⁸ is independently

-   -   methyl or ethyl.

Each R^(8a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(8a) is independently

-   -   C₁-C₄-alkyl.

Especially preferably, each R^(8a) is independently

-   -   methyl or ethyl.

Each R⁹ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁹ is independently

-   -   C₁-C₂-alkyl, C₁-C₂-haloalkyl.

Especially preferably, each R⁹ is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R^(9a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(9a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(9a) is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R¹⁰ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl, C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹⁰ is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₃-C₇-cycloalkyl.

Especially preferably, each R¹⁰ is independently

-   -   H or methyl.

Each R¹¹ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹¹ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl.

Especially preferably, each R¹¹ is independently

-   -   H, methyl or ethyl.

Each R^(11a) preferably is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₂-C₃-alkynyl.

More preferably, each R^(11a) is independently

-   -   H, C₁-C₄-alkyl, allyl or propargyl.

Especially preferably, each R^(11a) is independently

-   -   H, methyl or ethyl.

Each R¹² preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl.

More preferably, each R¹² is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹² is independently

-   -   H, methyl or ethyl.

Each R¹³ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl.

More preferably, each R¹³ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹³ is independently

-   -   methyl.

Each R¹⁴ preferably is independently

-   -   C₃-C₇-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) or        S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl, each substituted with 1 to 4 substituents        independently selected from the group consisting of cyano,        nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or        S(O)₂NR¹¹R¹²;    -   or phenyl, or a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄₋alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);

More preferably, each R¹⁴ is independently

-   -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Especially preferably, each R¹⁴ is independently

-   -   C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Each R¹⁵ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or phenyl optionally substituted with 1 to 5 substituents        independently selected from the group consisting of halogen,        cyano, OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,        S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, each R¹⁵ is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹⁵ is independently

-   -   methyl.

n preferably is 1, 2, 3 or 4. More preferably, n is 1, 2 or 3.Especially preferably, n is 1 or 2.

m preferably is 0, 1 or 2. More preferably, m is 0, 1 or 2. Especiallypreferably, m is 0 or 2.

X preferably is O or S. Especially preferably X is O.

Z preferably is O or S. Especially preferably Z is O.

In an individual type of this embodiment, Q is U-1. In anotherindividual type of this embodiment, Q is U-2. In another individual typeof this embodiment, Q is U-3. In another individual type of thisembodiment, Q is U-4. In another individual type of this embodiment, Qis U-5. In another individual type of this embodiment, Q is U-6. Inanother individual type of this embodiment, Q is U-7. In anotherindividual type of this embodiment, Q is U-8. In another individual typeof this embodiment, Q is U-9. In another individual type of thisembodiment, Q is U-10. In another individual type of this embodiment, Qis U-11. In another individual type of this embodiment, Q is U-12. Inanother individual type of this embodiment, Q is U-13. In anotherindividual type of this embodiment, Q is U-14. In another individualtype of this embodiment, Q is U-15. In another individual type of thisembodiment, Q is U-16. In another individual type of this embodiment, Qis U-17. In another individual type of this embodiment, Q is U-18. Inanother individual type of this embodiment, Q is U-19. In anotherindividual type of this embodiment, Q is U-20. In another individualtype of this embodiment, Q is U-21. In another individual type of thisembodiment, Q is U-22. In another individual type of this embodiment, Qis U-23. In another individual type of this embodiment, Q is U-24. Inanother individual type of this embodiment, Q is U-25. In anotherindividual type of this embodiment, Q is U-26. In another individualtype of this embodiment, Q is U-27. In another individual type of thisembodiment, Q is U-28. In another individual type of this embodiment, Qis U-29. In another individual type of this embodiment, Q is U-30. Inanother individual type of this embodiment, Q is U-31. In anotherindividual type of this embodiment, Q is U-32. In another individualtype of this embodiment, Q is U-33. In another individual type of thisembodiment, Q is U-34. In another individual type of this embodiment, Qis U-35. In another individual type of this embodiment, Q is U-36. Inanother individual type of this embodiment, Q is U-37. In anotherindividual type of this embodiment, Q is U-38. In another individualtype of this embodiment, Q is U-39. In another individual type of thisembodiment, Q is U-40. In another individual type of this embodiment, Qis U-41. In another individual type of this embodiment, Q is U-42. Inanother individual type of this embodiment, Q is U-43. In anotherindividual type of this embodiment, Q is U-44. In another individualtype of this embodiment, Q is U-45. In another individual type of thisembodiment, Q is U-46. In another individual type of this embodiment, Qis U-47. In another individual type of this embodiment, Q is U-48. Inanother individual type of this embodiment, Q is U-49. In anotherindividual type of this embodiment, Q is U-50. In another individualtype of this embodiment, Q is U-51. In another individual type of thisembodiment, Q is U-52. In another individual type of this embodiment, Qis U-53. In another individual type of this embodiment, Q is U-54. Inanother individual type of this embodiment, Q is U-55. In anotherindividual type of this embodiment, Q is U-56. In another individualtype of this embodiment, Q is U-57. In another individual type of thisembodiment, Q is U-58. In another individual type of this embodiment, Qis U-59. In another individual type of this embodiment, Q is U-60. Inanother individual type of this embodiment, Q is U-61. In anotherindividual type of this embodiment, Q is U-81. In another individualtype of this embodiment, Q is U-82. In another individual type of thisembodiment, Q is U-83. In another individual type of this embodiment, Qis U-84. In another individual type of this embodiment, Q is U-85. Inanother individual type of this embodiment, Q is U-86. In anotherindividual type of this embodiment, Q is U-87. In another individualtype of this embodiment, Q is U-89. In another individual type of thisembodiment, Q is U-90. In another individual type of this embodiment, Qis U-91. In another individual type of this embodiment, Q is U-92. Inanother individual type of this embodiment, Q is U-93. In anotherindividual type of this embodiment, Q is U-94. In another individualtype of this embodiment, Q is U-95. In another individual type of thisembodiment, Q is U-96. In another individual type of this embodiment, Qis U-97. In another individual type of this embodiment, Q is U-98. Inanother individual type of this embodiment, Q is U-99. In anotherindividual type of this embodiment, Q is U-100. In another individualtype of this embodiment, Q is U-101. In another individual type of thisembodiment, Q is U-102. In another individual type of this embodiment, Qis U-103. In another individual type of this embodiment, Q is U-105. Inanother individual type of this embodiment, Q is U-106. In anotherindividual type of this embodiment, Q is U-107. In another individualtype of this embodiment, Q is U-108. In another individual type of thisembodiment, Q is U-109. In another individual type of this embodiment, Qis U-110. In another individual type of this embodiment, Q is U-111. Inanother individual type of this embodiment, Q is U-112. In anotherindividual type of this embodiment, Q is U-113. In another individualtype of this embodiment, Q is U-114. In another individual type of thisembodiment, Q is U-115. In another individual type of this embodiment, Qis U-116. In another individual type of this embodiment, Q is U-117. Inanother individual type of this embodiment, Q is U-118. In anotherindividual type of this embodiment, Q is U-119. In another individualtype of this embodiment, Q is U-120. In another individual type of thisembodiment, Q is U-121. In another individual type of this embodiment, Qis U-122. In another individual type of this embodiment, Q is U-123.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), each R^(v) preferablyis independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹²;    -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹².

More preferably, each R^(v) is independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹².

Especially preferably, each R^(v) is independently

-   -   fluor, chlor, methoxy, trifluoromethyl, trifluoromethoxy or        methyl.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), r preferably is 0, 1,2, 3 or 4. More preferably, r is 0, 1, 2 or 3. Especially preferably, ris 1, 2 or 3.

Embodiment 5

The compounds of the invention are defined in general terms by theformula (I). In another preferred embodiment, the compounds of theinvention are defined by formula (Ie):

wherein

R¹, R², R³, R⁴, R^(4a), R⁵, R^(5a), R⁶, R^(6a), R⁷, R^(7a), R⁸, R^(8a),R⁹, R^(9a), R¹⁰, R¹¹, R^(11a), R¹², R¹³, R¹⁴, R¹⁵, Z, Q, R^(v), r, X, mand n are as defined above in the Summary of the Invention.

R¹ preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷,        N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹ or N(R¹⁰)S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, C(X)R⁷, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R¹ is

-   -   halogen, cyano, OR⁴, C₁-C₄-alkyl, C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;

Especially preferably, R¹ is

-   -   trifluoromethyl.

R² preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,        C₃-C₇-cycloalkyl, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R² is

-   -   H, halogen, cyano, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of cyano, OR⁴        and S(O)_(m)R⁹.

Especially preferably, R² is hydrogen.

R³ preferably is

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C(X)R⁷,        C(O)OR⁸ or C(O)NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, OR^(4a) and        S(O)_(m)R^(9a);    -   or C₁-C₄-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        C(X)R⁷ and C(O)OR⁸;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of phenyl or a        5- or 6-membered heteroaromatic ring, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴,        C₁-C₄-haloalkyl, C₂-C₆-alkoxyalkyl, C(X)R⁷, C(O)OR⁸, S(O)_(m)R⁹        and S(O)₂NR¹¹R¹².

More preferably, R³ is

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl, C(X)R⁷ or C(O)OR^(B);    -   or C₁-C₂-alkyl substituted with OR⁴;    -   or C₁-C₂-alkyl substituted with phenyl.

Especially preferably, R³ is hydrogen.

Q preferably is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₃-C₇-cycloalkyl, phenyl or a 5- or 6-membered heteroaromatic        ring system, each optionally substituted with 1 to 5        substituents independently selected from the group consisting of        halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹² and R¹⁴;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

More preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₇-cycloalkyl, phenyl or a 5-        or 6-membered heteroaromatic ring system, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹ and        S(O)₂NR¹¹R¹²;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

Even more preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₃-C₇-cycloalkyl;    -   or Q is selected from the group consisting of (U-1) to (U-61)        and (U-103).

Especially preferably, Q is methyl, ethyl or cyclopropyl or is selectedfrom the group consisting of (U-1), (U-49) and (U-103), particularly(U-1).

Each R⁴ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen.

More preferably, each R⁴ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R⁴ is independently methyl, ethyl, propyl,isopropyl, difluoromethyl or trifluoromethyl.

Each R^(4a) preferably is independently

-   -   H, C₁-C₆-alkyl or C₁-C₆-haloalkyl.

More preferably, each R^(4a) is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R^(4a) is independently

-   -   methyl or ethyl.

Each R⁵ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl;        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁵ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹².

Especially preferably, each R⁵ is independently

-   -   H, methyl or ethyl.

Each R^(5a) preferably is independently

-   -   H or C₁-C₄-alkyl.

More preferably, each R^(5a) is independently

-   -   H or C₁-C₂-alkyl.

Especially preferably, each R^(5a) is independently

-   -   methyl or ethyl.

Each R⁶ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl or C₂-C₄-haloalkynyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁶ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl or        C₂-C₄-haloalkenyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

Especially preferably, each R⁶ is independently

-   -   H, methyl or ethyl.

Each R^(6a) preferably is independently

-   -   H, C₁-C₄-alkyl, C(O)R¹³ or C(O)OR¹³.

More preferably, each R^(6a) is independently

-   -   H or C₁-C₄-alkyl.

Especially preferably, each R^(6a) is independently

-   -   H, methyl or ethyl.

Each R⁷ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or        C₂-C₆-haloalkenyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁷ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₂-alkyl and C₁-C₂-haloalkyl.

Especially preferably, each R⁷ is independently

-   -   H, methyl, ethyl or trifluoromethyl.

Each R^(7a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(7a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(7a) is independently

-   -   methyl or ethyl.

Each R⁸ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁸ is independently

-   -   C₁-C₂-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R⁸ is independently

-   -   methyl or ethyl.

Each R^(8a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(8a) is independently

-   -   C₁-C₄-alkyl.

Especially preferably, each R^(8a) is independently

-   -   methyl or ethyl.

Each R⁹ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁹ is independently

-   -   C₁-C₂-alkyl, C₁-C₂-haloalkyl.

Especially preferably, each R⁹ is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R^(9a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(9a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(9a) is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R¹⁰ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl, C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹⁰ is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₃-C₇-cycloalkyl.

Especially preferably, each R¹⁰ is independently

-   -   H or methyl.

Each R¹¹ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹¹ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl.

Especially preferably, each R¹¹ is independently

-   -   H, methyl or ethyl.

Each R^(11a) preferably is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₂-C₃-alkynyl.

More preferably, each R^(11a) is independently

-   -   H, C₁-C₄-alkyl, allyl or propargyl.

Especially preferably, each R^(11a) is independently

-   -   H, methyl or ethyl.

Each R¹² preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl.

More preferably, each R¹² is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹² is independently

-   -   H, methyl or ethyl.

Each R¹³ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl.

More preferably, each R¹³ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹³ is independently

-   -   methyl.

Each R¹⁴ preferably is independently

-   -   C₃-C₇-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) or        S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl, each substituted with 1 to 4 substituents        independently selected from the group consisting of cyano,        nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or        S(O)₂NR¹¹R¹²;    -   or phenyl, or a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄₋alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);

More preferably, each R¹⁴ is independently

-   -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Especially preferably, each R¹⁴ is independently

-   -   C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Each R¹⁵ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or phenyl optionally substituted with 1 to 5 substituents        independently selected from the group consisting of halogen,        cyano, OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,        S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, each R¹⁵ is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹⁵ is independently

-   -   methyl.

n preferably is 1, 2, 3 or 4. More preferably, n is 1, 2 or 3.Especially preferably, n is 1 or 2.

m preferably is 0, 1 or 2. More preferably, m is 0, 1 or 2. Especiallypreferably, m is 0 or 2.

X preferably is O or S. Especially preferably X is O.

Z preferably is O or S. Especially preferably Z is O.

In an individual type of this embodiment, Q is U-1. In anotherindividual type of this embodiment, Q is U-2. In another individual typeof this embodiment, Q is U-3. In another individual type of thisembodiment, Q is U-4. In another individual type of this embodiment, Qis U-5. In another individual type of this embodiment, Q is U-6. Inanother individual type of this embodiment, Q is U-7. In anotherindividual type of this embodiment, Q is U-8. In another individual typeof this embodiment, Q is U-9. In another individual type of thisembodiment, Q is U-10. In another individual type of this embodiment, Qis U-11. In another individual type of this embodiment, Q is U-12. Inanother individual type of this embodiment, Q is U-13. In anotherindividual type of this embodiment, Q is U-14. In another individualtype of this embodiment, Q is U-15. In another individual type of thisembodiment, Q is U-16. In another individual type of this embodiment, Qis U-17. In another individual type of this embodiment, Q is U-18. Inanother individual type of this embodiment, Q is U-19. In anotherindividual type of this embodiment, Q is U-20. In another individualtype of this embodiment, Q is U-21. In another individual type of thisembodiment, Q is U-22. In another individual type of this embodiment, Qis U-23. In another individual type of this embodiment, Q is U-24. Inanother individual type of this embodiment, Q is U-25. In anotherindividual type of this embodiment, Q is U-26. In another individualtype of this embodiment, Q is U-27. In another individual type of thisembodiment, Q is U-28. In another individual type of this embodiment, Qis U-29. In another individual type of this embodiment, Q is U-30. Inanother individual type of this embodiment, Q is U-31. In anotherindividual type of this embodiment, Q is U-32. In another individualtype of this embodiment, Q is U-33. In another individual type of thisembodiment, Q is U-34. In another individual type of this embodiment, Qis U-35. In another individual type of this embodiment, Q is U-36. Inanother individual type of this embodiment, Q is U-37. In anotherindividual type of this embodiment, Q is U-38. In another individualtype of this embodiment, Q is U-39. In another individual type of thisembodiment, Q is U-40. In another individual type of this embodiment, Qis U-41. In another individual type of this embodiment, Q is U-42. Inanother individual type of this embodiment, Q is U-43. In anotherindividual type of this embodiment, Q is U-44. In another individualtype of this embodiment, Q is U-45. In another individual type of thisembodiment, Q is U-46. In another individual type of this embodiment, Qis U-47. In another individual type of this embodiment, Q is U-48. Inanother individual type of this embodiment, Q is U-49. In anotherindividual type of this embodiment, Q is U-50. In another individualtype of this embodiment, Q is U-51. In another individual type of thisembodiment, Q is U-52. In another individual type of this embodiment, Qis U-53. In another individual type of this embodiment, Q is U-54. Inanother individual type of this embodiment, Q is U-55. In anotherindividual type of this embodiment, Q is U-56. In another individualtype of this embodiment, Q is U-57. In another individual type of thisembodiment, Q is U-58. In another individual type of this embodiment, Qis U-59. In another individual type of this embodiment, Q is U-60. Inanother individual type of this embodiment, Q is U-61. In anotherindividual type of this embodiment, Q is U-81. In another individualtype of this embodiment, Q is U-82. In another individual type of thisembodiment, Q is U-83. In another individual type of this embodiment, Qis U-84. In another individual type of this embodiment, Q is U-85. Inanother individual type of this embodiment, Q is U-86. In anotherindividual type of this embodiment, Q is U-87. In another individualtype of this embodiment, Q is U-89. In another individual type of thisembodiment, Q is U-90. In another individual type of this embodiment, Qis U-91. In another individual type of this embodiment, Q is U-92. Inanother individual type of this embodiment, Q is U-93. In anotherindividual type of this embodiment, Q is U-94. In another individualtype of this embodiment, Q is U-95. In another individual type of thisembodiment, Q is U-96. In another individual type of this embodiment, Qis U-97. In another individual type of this embodiment, Q is U-98. Inanother individual type of this embodiment, Q is U-99. In anotherindividual type of this embodiment, Q is U-100. In another individualtype of this embodiment, Q is U-101. In another individual type of thisembodiment, Q is U-102. In another individual type of this embodiment, Qis U-103. In another individual type of this embodiment, Q is U-105. Inanother individual type of this embodiment, Q is U-106. In anotherindividual type of this embodiment, Q is U-107. In another individualtype of this embodiment, Q is U-108. In another individual type of thisembodiment, Q is U-109. In another individual type of this embodiment, Qis U-110. In another individual type of this embodiment, Q is U-111. Inanother individual type of this embodiment, Q is U-112. In anotherindividual type of this embodiment, Q is U-113. In another individualtype of this embodiment, Q is U-114. In another individual type of thisembodiment, Q is U-115. In another individual type of this embodiment, Qis U-116. In another individual type of this embodiment, Q is U-117. Inanother individual type of this embodiment, Q is U-118. In anotherindividual type of this embodiment, Q is U-119. In another individualtype of this embodiment, Q is U-120. In another individual type of thisembodiment, Q is U-121. In another individual type of this embodiment, Qis U-122. In another individual type of this embodiment, Q is U-123.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), each R^(v) preferablyis independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹²;    -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹².

More preferably, each R^(v) is independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹².

Especially preferably, each R^(v) is independently

-   -   fluor, chlor, methoxy, trifluoromethyl, trifluoromethoxy or        methyl.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), r preferably is 0, 1,2, 3 or 4. More preferably, r is 0, 1, 2 or 3. Especially preferably, ris 1, 2 or 3.

Embodiment 6

The compounds of the invention are defined in general terms by theformula (I). In another preferred embodiment, the compounds of theinvention are defined by formula (If):

wherein

R¹, R², R³, R⁴, R^(4a), R⁵, R^(5a), R⁶, R^(6a), R⁷, R^(7a), R⁸, R^(8a),R⁹, R^(9a), R¹⁰, R¹¹, R^(11a), R¹², R¹³, R¹⁴, R¹⁵, Z, Q, R^(v), r, X, mand n are as defined above in the Summary of the Invention.

R¹ preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷,        N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹ or N(R¹⁰)S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl, C₄-C₈-cycloalkylalkyl,        C₆-C₁₄-cycloalkylcycloalkyl or C₅-C₇-cycloalkenyl, each        optionally substituted with 1 to 4 substituents independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, C(X)R⁷, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R¹ is

-   -   halogen, cyano, OR⁴, C₁-C₄-alkyl, C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;

Especially preferably, R¹ is

-   -   chlorine or trifluoromethyl.

R² preferably is

-   -   H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆-alkyl,        C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,        C₃-C₇-cycloalkyl, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₆-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        NR⁵ R⁶, S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, R² is

-   -   H, halogen, cyano, S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;    -   or C₃-C₆-cycloalkyl, optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of cyano, OR⁴        and S(O)_(m)R⁹.

Especially preferably, R² is hydrogen.

R³ preferably is

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C(X)R⁷,        C(O)OR⁸ or C(O)NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, OR^(4a) and        S(O)_(m)R^(9a);    -   or C₁-C₄-alkyl substituted with 1 to 4 substituents        independently selected from the group consisting of cyano, OR⁴,        C(X)R⁷ and C(O)OR⁸;    -   or C₁-C₄-alkyl substituted with 1 to 2 substituents        independently selected from the group consisting of phenyl or a        5- or 6-membered heteroaromatic ring, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴,        C₁-C₄-haloalkyl, C₂-C₆-alkoxyalkyl, C(X)R⁷, C(O)OR⁸, S(O)_(m)R⁹        and S(O)₂NR¹¹R¹².

More preferably, R³ is

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl, C(X)R⁷ or C(O)OR⁸;    -   or C₁-C₂-alkyl substituted with OR⁴;    -   or C₁-C₂-alkyl substituted with phenyl.

Especially preferably, R³ is hydrogen.

Q preferably is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₃-C₇-cycloalkyl, phenyl or a 5- or 6-membered heteroaromatic        ring system, each optionally substituted with 1 to 5        substituents independently selected from the group consisting of        halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹² and R¹⁴;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

More preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₇-cycloalkyl, phenyl or a 5-        or 6-membered heteroaromatic ring system, each optionally        substituted with 1 to 5 substituents independently selected from        the group consisting of halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹ and        S(O)₂NR¹¹R¹²;    -   or Q is selected from the group consisting of (U-1) to (U-61),        (U-81) to (U-87), (U-89) to (U-103) and (U-105) to (U-123).

Even more preferably, Q is

-   -   C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₃-C₇-cycloalkyl;    -   or Q is selected from the group consisting of (U-1) to (U-61)        and (U-103).

Especially preferably, Q is methyl, ethyl or cyclopropyl or is selectedfrom the group consisting of (U-1), (U-49) and (U-103), particularly(U-1).

Each R⁴ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen.

More preferably, each R⁴ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R⁴ is independently methyl, ethyl, propyl,isopropyl, difluoromethyl or trifluoromethyl.

Each R^(4a) preferably is independently

-   -   H, C₁-C₆-alkyl or C₁-C₆-haloalkyl.

More preferably, each R^(4a) is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R^(4a) is independently

-   -   methyl or ethyl.

Each R⁵ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹²;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl;        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁵ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, S(O)_(m)R⁹        or S(O)₂NR¹¹R¹².

Especially preferably, each R⁵ is independently

-   -   H, methyl or ethyl.

Each R^(5a) preferably is independently

-   -   H or C₁-C₄-alkyl.

More preferably, each R^(5a) is independently

-   -   H or C₁-C₂-alkyl.

Especially preferably, each R^(5a) is independently

-   -   methyl or ethyl.

Each R⁶ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl or C₂-C₄-haloalkynyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁶ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl or        C₂-C₄-haloalkenyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

Especially preferably, each R⁶ is independently

-   -   H, methyl or ethyl.

Each R^(6a) preferably is independently

-   -   H, C₁-C₄-alkyl, C(O)R¹³ or C(O)OR¹³.

More preferably, each R^(6a) is independently

-   -   H or C₁-C₄-alkyl.

Especially preferably, each R^(6a) is independently

-   -   H, methyl or ethyl.

Each R⁷ preferably is independently

-   -   H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or        C₂-C₆-haloalkenyl;    -   or C₃-C₇-cycloalkyl or C₄-C₈-cycloalkylalkyl, each optionally        substituted with 1 to 4 substituents independently selected from        the group consisting of halogen, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

More preferably, each R⁷ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or C₃-C₇-cycloalkyl optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₂-alkyl and C₁-C₂-haloalkyl.

Especially preferably, each R⁷ is independently

-   -   H, methyl, ethyl or trifluoromethyl.

Each R^(7a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(7a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(7a) is independently

-   -   methyl or ethyl.

Each R⁸ preferably is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁸ is independently

-   -   C₁-C₂-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R⁸ is independently

-   -   methyl or ethyl.

Each R^(8a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(8a) is independently

-   -   C₁-C₄-alkyl.

Especially preferably, each R^(8a) is independently

-   -   methyl or ethyl.

Each R⁹ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R⁹ is independently

-   -   C₁-C₂-alkyl, C₁-C₂-haloalkyl.

Especially preferably, each R⁹ is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R^(9a) preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

More preferably, each R^(9a) is independently

-   -   C₁-C₄-alkyl or C₁-C₂-haloalkyl.

Especially preferably, each R^(9a) is independently

-   -   methyl, ethyl or trifluoromethyl.

Each R¹⁰ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl, C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹⁰ is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₃-C₇-cycloalkyl.

Especially preferably, each R¹⁰ is independently

-   -   H or methyl.

Each R¹¹ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂-C₃-haloalkynyl or        C₃-C₇-cycloalkyl.

More preferably, each R¹¹ is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl.

Especially preferably, each R¹¹ is independently

-   -   H, methyl or ethyl.

Each R^(11a) preferably is independently

-   -   H, C₁-C₄-alkyl, C₂-C₃-alkenyl or C₂-C₃-alkynyl.

More preferably, each R^(11a) is independently

-   -   H, C₁-C₄-alkyl, allyl or propargyl.

Especially preferably, each R^(11a) is independently

-   -   H, methyl or ethyl.

Each R¹² preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂—C haloalkynyl.

More preferably, each R¹² is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹² is independently

-   -   H, methyl or ethyl.

Each R¹³ preferably is independently

-   -   H, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl,        C₂-C₃-haloalkenyl, C₂-C₃-alkynyl or C₂—C haloalkynyl.

More preferably, each R¹³ is independently

-   -   H, C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹³ is independently

-   -   methyl.

Each R¹⁴ preferably is independently

-   -   C₃-C₇-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, OR^(4a) or        S(O)_(m)R^(9a);    -   or C₁-C₆-alkyl, each substituted with 1 to 4 substituents        independently selected from the group consisting of cyano,        nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or        S(O)₂NR¹¹R¹²;    -   or phenyl, or a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄₋alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₆-alkoxyalkyl, C(X)R⁷,        C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or        N(R¹⁰)C(O)R^(7a);

More preferably, each R¹⁴ is independently

-   -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Especially preferably, each R¹⁴ is independently

-   -   C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²;

Each R¹⁵ preferably is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   or phenyl optionally substituted with 1 to 5 substituents        independently selected from the group consisting of halogen,        cyano, OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,        S(O)_(m)R⁹ and S(O)₂NR¹¹R¹².

More preferably, each R¹⁵ is independently

-   -   C₁-C₄-alkyl or C₁-C₄-haloalkyl.

Especially preferably, each R¹⁵ is independently

-   -   methyl.

n preferably is 1, 2, 3 or 4. More preferably, n is 1, 2 or 3.Especially preferably, n is 1 or 2.

m preferably is 0, 1 or 2. More preferably, m is 0, 1 or 2. Especiallypreferably, m is 0 or 2.

X preferably is O or S. Especially preferably X is O.

Z preferably is O or S. Especially preferably Z is O.

In an individual type of this embodiment, Q is U-1. In anotherindividual type of this embodiment, Q is U-2. In another individual typeof this embodiment, Q is U-3. In another individual type of thisembodiment, Q is U-4. In another individual type of this embodiment, Qis U-5. In another individual type of this embodiment, Q is U-6. Inanother individual type of this embodiment, Q is U-7. In anotherindividual type of this embodiment, Q is U-8. In another individual typeof this embodiment, Q is U-9. In another individual type of thisembodiment, Q is U-10. In another individual type of this embodiment, Qis U-11. In another individual type of this embodiment, Q is U-12. Inanother individual type of this embodiment, Q is U-13. In anotherindividual type of this embodiment, Q is U-14. In another individualtype of this embodiment, Q is U-15. In another individual type of thisembodiment, Q is U-16. In another individual type of this embodiment, Qis U-17. In another individual type of this embodiment, Q is U-18. Inanother individual type of this embodiment, Q is U-19. In anotherindividual type of this embodiment, Q is U-20. In another individualtype of this embodiment, Q is U-21. In another individual type of thisembodiment, Q is U-22. In another individual type of this embodiment, Qis U-23. In another individual type of this embodiment, Q is U-24. Inanother individual type of this embodiment, Q is U-25. In anotherindividual type of this embodiment, Q is U-26. In another individualtype of this embodiment, Q is U-27. In another individual type of thisembodiment, Q is U-28. In another individual type of this embodiment, Qis U-29. In another individual type of this embodiment, Q is U-30. Inanother individual type of this embodiment, Q is U-31. In anotherindividual type of this embodiment, Q is U-32. In another individualtype of this embodiment, Q is U-33. In another individual type of thisembodiment, Q is U-34. In another individual type of this embodiment, Qis U-35. In another individual type of this embodiment, Q is U-36. Inanother individual type of this embodiment, Q is U-37. In anotherindividual type of this embodiment, Q is U-38. In another individualtype of this embodiment, Q is U-39. In another individual type of thisembodiment, Q is U-40. In another individual type of this embodiment, Qis U-41. In another individual type of this embodiment, Q is U-42. Inanother individual type of this embodiment, Q is U-43. In anotherindividual type of this embodiment, Q is U-44. In another individualtype of this embodiment, Q is U-45. In another individual type of thisembodiment, Q is U-46. In another individual type of this embodiment, Qis U-47. In another individual type of this embodiment, Q is U-48. Inanother individual type of this embodiment, Q is U-49. In anotherindividual type of this embodiment, Q is U-50. In another individualtype of this embodiment, Q is U-51. In another individual type of thisembodiment, Q is U-52. In another individual type of this embodiment, Qis U-53. In another individual type of this embodiment, Q is U-54. Inanother individual type of this embodiment, Q is U-55. In anotherindividual type of this embodiment, Q is U-56. In another individualtype of this embodiment, Q is U-57. In another individual type of thisembodiment, Q is U-58. In another individual type of this embodiment, Qis U-59. In another individual type of this embodiment, Q is U-60. Inanother individual type of this embodiment, Q is U-61. In anotherindividual type of this embodiment, Q is U-81. In another individualtype of this embodiment, Q is U-82. In another individual type of thisembodiment, Q is U-83. In another individual type of this embodiment, Qis U-84. In another individual type of this embodiment, Q is U-85. Inanother individual type of this embodiment, Q is U-86. In anotherindividual type of this embodiment, Q is U-87. In another individualtype of this embodiment, Q is U-89. In another individual type of thisembodiment, Q is U-90. In another individual type of this embodiment, Qis U-91. In another individual type of this embodiment, Q is U-92. Inanother individual type of this embodiment, Q is U-93. In anotherindividual type of this embodiment, Q is U-94. In another individualtype of this embodiment, Q is U-95. In another individual type of thisembodiment, Q is U-96. In another individual type of this embodiment, Qis U-97. In another individual type of this embodiment, Q is U-98. Inanother individual type of this embodiment, Q is U-99. In anotherindividual type of this embodiment, Q is U-100. In another individualtype of this embodiment, Q is U-101. In another individual type of thisembodiment, Q is U-102. In another individual type of this embodiment, Qis U-103. In another individual type of this embodiment, Q is U-105. Inanother individual type of this embodiment, Q is U-106. In anotherindividual type of this embodiment, Q is U-107. In another individualtype of this embodiment, Q is U-108. In another individual type of thisembodiment, Q is U-109. In another individual type of this embodiment, Qis U-110. In another individual type of this embodiment, Q is U-111. Inanother individual type of this embodiment, Q is U-112. In anotherindividual type of this embodiment, Q is U-113. In another individualtype of this embodiment, Q is U-114. In another individual type of thisembodiment, Q is U-115. In another individual type of this embodiment, Qis U-116. In another individual type of this embodiment, Q is U-117. Inanother individual type of this embodiment, Q is U-118. In anotherindividual type of this embodiment, Q is U-119. In another individualtype of this embodiment, Q is U-120. In another individual type of thisembodiment, Q is U-121. In another individual type of this embodiment, Qis U-122. In another individual type of this embodiment, Q is U-123.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), each R^(v) preferablyis independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹,        S(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹,        N(R¹⁰)S(O)₂NR¹¹R¹²;    -   C₃-C₆-cycloalkyl, each optionally substituted with 1 to 4        substituents independently selected from the group consisting of        halogen or C₁-C₄-alkyl;    -   or C₁-C₆-alkyl, each substituted with 1 to 2 substituents        independently selected from the group consisting of OR⁴;    -   or C₁-C₆-alkyl substituted with a substituent selected from the        group consisting of a 5- or 6-membered heteroaromatic ring, each        optionally substituted with 1 to 5 substituents independently        selected from the group consisting of halogen, cyano, nitro,        OR⁴, NR⁵R⁶, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C(X)R⁷, C(O)OR⁸,        C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹².

More preferably, each R^(v) is independently

-   -   halogen, cyano, nitro, OR⁴, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹².

Especially preferably, each R^(v) is independently

-   -   fluor, chlor, methoxy, trifluoromethyl, trifluoromethoxy or        methyl.

In all cases with Q is defined to be one of (U-1) to (U-61), (U-81) to(U-87), (U-89) to (U-103) or (U-105) to (U-123), r preferably is 0, 1,2, 3 or 4. More preferably, r is 0, 1, 2 or 3. Especially preferably, ris 1, 2 or 3.

A specific aspect of the compounds of this embodiment are compoundswhich are represented by formula (If-1)

wherein the structural elements are defined as given above forembodiment 6.

The definitions of radicals, and explanations, that are given above ingeneral or in ranges of preference may be combined arbitrarily with oneanother, thus including combinations between the respective ranges andranges of preference. The definitions and explanations apply to the endproducts and also to the precursors and intermediates accordingly.

Preferred in accordance with the invention are the compounds of theformula (I) in which each structural element is defined as given aboveas being preferred (“preferably”). For those structural elements lackingthe preferred definition, the definition in the summary of the inventionshall apply.

Likewise preferred in accordance with the invention are the compounds ofthe formula (I) in which Q is selected from the group consisting of(U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and (U-105) to(U-123) and in which each further structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

More preferred in accordance with the invention are the compounds of theformula (I) in which each structural element is defined as given aboveas being more preferred (“more preferably”). For those structuralelements lacking the more preferred definition, the definition givenabove as being especially preferred (“especially preferably”) shallapply with the proviso that for those structural elements lacking theespecially preferred definition as well, the definition in the summaryof the invention shall apply.

Likewise more preferred in accordance with the invention are thecompounds of the formula (I) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being more preferred (“more preferably”). Forthose structural elements lacking the more preferred definition, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Even more preferred in accordance with the invention are the compoundsof the formula (I) in which each structural element is defined as givenabove as being even more preferred (“even more preferably”). For thosestructural elements lacking the even more preferred definition, thedefinition given above as being more preferred (“more preferably”) shallapply with the proviso that for those structural elements lacking themore preferred definition as well, the definition given above as beingespecially preferred (“especially preferably”) shall apply with theproviso that for those structural elements lacking the especiallypreferred definition as well, the definition in the summary of theinvention shall apply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (I) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being more preferred(“more preferably”) shall apply with the proviso that for thosestructural elements lacking the more preferred definition as well, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Alternatively, even more preferred in accordance with the invention arethe compounds of the formula (I) in which each structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (I) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Especially preferred in accordance with the invention are the compoundsof the formula (I) in which each structural element is defined as givenabove as being especially preferred (especially preferably). For thosestructural elements lacking the especially preferred definition, thedefinition in the summary of the invention shall apply.

Likewise especially preferred in accordance with the invention are thecompounds of the formula (I) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being especially preferred (especiallypreferably). For those structural elements lacking the especiallypreferred definition, the definition in the summary of the inventionshall apply.

With regard to embodiment 1 as defined above, the following applies:

Preferred in accordance with the invention are the compounds of theformula (Ia) in which each structural element is defined as given aboveas being preferred (“preferably”). For those structural elements lackingthe preferred definition, the definition in the summary of the inventionshall apply.

Likewise preferred in accordance with the invention are the compounds ofthe formula (Ia) in which Q is selected from the group consisting of(U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and (U-105) to(U-123) and in which each further structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

More preferred in accordance with the invention are the compounds of theformula (Ia) in which each structural element is defined as given aboveas being more preferred (“more preferably”). For those structuralelements lacking the more preferred definition, the definition givenabove as being especially preferred (“especially preferably”) shallapply with the proviso that for those structural elements lacking theespecially preferred definition as well, the definition in the summaryof the invention shall apply.

Likewise more preferred in accordance with the invention are thecompounds of the formula (Ia) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being more preferred (“more preferably”). Forthose structural elements lacking the more preferred definition, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Even more preferred in accordance with the invention are the compoundsof the formula (Ia) in which each structural element is defined as givenabove as being even more preferred (“even more preferably”). For thosestructural elements lacking the even more preferred definition, thedefinition given above as being more preferred (“more preferably”) shallapply with the proviso that for those structural elements lacking themore preferred definition as well, the definition given above as beingespecially preferred (“especially preferably”) shall apply with theproviso that for those structural elements lacking the especiallypreferred definition as well, the definition in the summary of theinvention shall apply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Ia) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being more preferred(“more preferably”) shall apply with the proviso that for thosestructural elements lacking the more preferred definition as well, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Alternatively, even more preferred in accordance with the invention arethe compounds of the formula (Ia) in which each structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Ia) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Especially preferred in accordance with the invention are the compoundsof the formula (Ia) in which each structural element is defined as givenabove as being especially preferred (especially preferably). For thosestructural elements lacking the especially preferred definition, thedefinition in the summary of the invention shall apply.

Likewise especially preferred in accordance with the invention are thecompounds of the formula (Ia) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being especially preferred (especiallypreferably). For those structural elements lacking the especiallypreferred definition, the definition in the summary of the inventionshall apply.

With regard to embodiment 2 as defined above, the following applies:

Preferred in accordance with the invention are the compounds of theformula (Ib) in which each structural element is defined as given aboveas being preferred (“preferably”). For those structural elements lackingthe preferred definition, the definition in the summary of the inventionshall apply.

Likewise preferred in accordance with the invention are the compounds ofthe formula (Ib) in which Q is selected from the group consisting of(U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and (U-105) to(U-123) and in which each further structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

More preferred in accordance with the invention are the compounds of theformula (Ib) in which each structural element is defined as given aboveas being more preferred (“more preferably”). For those structuralelements lacking the more preferred definition, the definition givenabove as being especially preferred (“especially preferably”) shallapply with the proviso that for those structural elements lacking theespecially preferred definition as well, the definition in the summaryof the invention shall apply.

Likewise more preferred in accordance with the invention are thecompounds of the formula (Ib) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being more preferred (“more preferably”). Forthose structural elements lacking the more preferred definition, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Even more preferred in accordance with the invention are the compoundsof the formula (Ib) in which each structural element is defined as givenabove as being even more preferred (“even more preferably”). For thosestructural elements lacking the even more preferred definition, thedefinition given above as being more preferred (“more preferably”) shallapply with the proviso that for those structural elements lacking themore preferred definition as well, the definition given above as beingespecially preferred (“especially preferably”) shall apply with theproviso that for those structural elements lacking the especiallypreferred definition as well, the definition in the summary of theinvention shall apply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Ib) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being more preferred(“more preferably”) shall apply with the proviso that for thosestructural elements lacking the more preferred definition as well, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Alternatively, even more preferred in accordance with the invention arethe compounds of the formula (Ib) in which each structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Ib) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Especially preferred in accordance with the invention are the compoundsof the formula (Ib) in which each structural element is defined as givenabove as being especially preferred (especially preferably). For thosestructural elements lacking the especially preferred definition, thedefinition in the summary of the invention shall apply.

Likewise especially preferred in accordance with the invention are thecompounds of the formula (Ib) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being especially preferred (especiallypreferably). For those structural elements lacking the especiallypreferred definition, the definition in the summary of the inventionshall apply.

With regard to embodiment 3 as defined above, the following applies:

Preferred in accordance with the invention are the compounds of theformula (Ic) in which each structural element is defined as given aboveas being preferred (“preferably”). For those structural elements lackingthe preferred definition, the definition in the summary of the inventionshall apply.

Likewise preferred in accordance with the invention are the compounds ofthe formula (Ic) in which Q is selected from the group consisting of(U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and (U-105) to(U-123) and in which each further structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

More preferred in accordance with the invention are the compounds of theformula (Ic) in which each structural element is defined as given aboveas being more preferred (“more preferably”). For those structuralelements lacking the more preferred definition, the definition givenabove as being especially preferred (“especially preferably”) shallapply with the proviso that for those structural elements lacking theespecially preferred definition as well, the definition in the summaryof the invention shall apply.

Likewise more preferred in accordance with the invention are thecompounds of the formula (Ic) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being more preferred (“more preferably”). Forthose structural elements lacking the more preferred definition, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Even more preferred in accordance with the invention are the compoundsof the formula (Ic) in which each structural element is defined as givenabove as being even more preferred (“even more preferably”). For thosestructural elements lacking the even more preferred definition, thedefinition given above as being more preferred (“more preferably”) shallapply with the proviso that for those structural elements lacking themore preferred definition as well, the definition given above as beingespecially preferred (“especially preferably”) shall apply with theproviso that for those structural elements lacking the especiallypreferred definition as well, the definition in the summary of theinvention shall apply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Ic) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being more preferred(“more preferably”) shall apply with the proviso that for thosestructural elements lacking the more preferred definition as well, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Alternatively, even more preferred in accordance with the invention arethe compounds of the formula (Ic) in which each structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Ic) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Especially preferred in accordance with the invention are the compoundsof the formula (Ic) in which each structural element is defined as givenabove as being especially preferred (especially preferably). For thosestructural elements lacking the especially preferred definition, thedefinition in the summary of the invention shall apply.

Likewise especially preferred in accordance with the invention are thecompounds of the formula (Ic) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being especially preferred (especiallypreferably). For those structural elements lacking the especiallypreferred definition, the definition in the summary of the inventionshall apply.

With regard to embodiment 4 as defined above, the following applies:

Preferred in accordance with the invention are the compounds of theformula (Id) in which each structural element is defined as given aboveas being preferred (“preferably”). For those structural elements lackingthe preferred definition, the definition in the summary of the inventionshall apply.

Likewise preferred in accordance with the invention are the compounds ofthe formula (Id) in which Q is selected from the group consisting of(U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and (U-105) to(U-123) and in which each further structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

More preferred in accordance with the invention are the compounds of theformula (Id) in which each structural element is defined as given aboveas being more preferred (“more preferably”). For those structuralelements lacking the more preferred definition, the definition givenabove as being especially preferred (“especially preferably”) shallapply with the proviso that for those structural elements lacking theespecially preferred definition as well, the definition in the summaryof the invention shall apply.

Likewise more preferred in accordance with the invention are thecompounds of the formula (Id) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being more preferred (“more preferably”). Forthose structural elements lacking the more preferred definition, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Even more preferred in accordance with the invention are the compoundsof the formula (Id) in which each structural element is defined as givenabove as being even more preferred (“even more preferably”). For thosestructural elements lacking the even more preferred definition, thedefinition given above as being more preferred (“more preferably”) shallapply with the proviso that for those structural elements lacking themore preferred definition as well, the definition given above as beingespecially preferred (“especially preferably”) shall apply with theproviso that for those structural elements lacking the especiallypreferred definition as well, the definition in the summary of theinvention shall apply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Id) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being more preferred(“more preferably”) shall apply with the proviso that for thosestructural elements lacking the more preferred definition as well, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Alternatively, even more preferred in accordance with the invention arethe compounds of the formula (Id) in which each structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Id) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Especially preferred in accordance with the invention are the compoundsof the formula (Id) in which each structural element is defined as givenabove as being especially preferred (especially preferably). For thosestructural elements lacking the especially preferred definition, thedefinition in the summary of the invention shall apply.

Likewise especially preferred in accordance with the invention are thecompounds of the formula (Id) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being especially preferred (especiallypreferably). For those structural elements lacking the especiallypreferred definition, the definition in the summary of the inventionshall apply.

With regard to embodiment 5 as defined above, the following applies:

Preferred in accordance with the invention are the compounds of theformula (Ie) in which each structural element is defined as given aboveas being preferred (“preferably”). For those structural elements lackingthe preferred definition, the definition in the summary of the inventionshall apply.

Likewise preferred in accordance with the invention are the compounds ofthe formula (Ie) in which Q is selected from the group consisting of(U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and (U-105) to(U-123) and in which each further structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

More preferred in accordance with the invention are the compounds of theformula (Ie) in which each structural element is defined as given aboveas being more preferred (“more preferably”). For those structuralelements lacking the more preferred definition, the definition givenabove as being especially preferred (“especially preferably”) shallapply with the proviso that for those structural elements lacking theespecially preferred definition as well, the definition in the summaryof the invention shall apply.

Likewise more preferred in accordance with the invention are thecompounds of the formula (Ie) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being more preferred (“more preferably”). Forthose structural elements lacking the more preferred definition, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Even more preferred in accordance with the invention are the compoundsof the formula (Ie) in which each structural element is defined as givenabove as being even more preferred (“even more preferably”). For thosestructural elements lacking the even more preferred definition, thedefinition given above as being more preferred (“more preferably”) shallapply with the proviso that for those structural elements lacking themore preferred definition as well, the definition given above as beingespecially preferred (“especially preferably”) shall apply with theproviso that for those structural elements lacking the especiallypreferred definition as well, the definition in the summary of theinvention shall apply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Ie) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being more preferred(“more preferably”) shall apply with the proviso that for thosestructural elements lacking the more preferred definition as well, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Alternatively, even more preferred in accordance with the invention arethe compounds of the formula (Ie) in which each structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Ie) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Especially preferred in accordance with the invention are the compoundsof the formula (Ie) in which each structural element is defined as givenabove as being especially preferred (especially preferably). For thosestructural elements lacking the especially preferred definition, thedefinition in the summary of the invention shall apply.

Likewise especially preferred in accordance with the invention are thecompounds of the formula (Ie) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being especially preferred (especiallypreferably). For those structural elements lacking the especiallypreferred definition, the definition in the summary of the inventionshall apply.

With regard to embodiment 6 as defined above, the following applies:

Preferred in accordance with the invention are the compounds of theformula (If) in which each structural element is defined as given aboveas being preferred (“preferably”). For those structural elements lackingthe preferred definition, the definition in the summary of the inventionshall apply.

Likewise preferred in accordance with the invention are the compounds ofthe formula (If) in which Q is selected from the group consisting of(U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and (U-105) to(U-123) and in which each further structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

More preferred in accordance with the invention are the compounds of theformula (If) in which each structural element is defined as given aboveas being more preferred (“more preferably”). For those structuralelements lacking the more preferred definition, the definition givenabove as being especially preferred (“especially preferably”) shallapply with the proviso that for those structural elements lacking theespecially preferred definition as well, the definition in the summaryof the invention shall apply.

Likewise more preferred in accordance with the invention are thecompounds of the formula (If) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being more preferred (“more preferably”). Forthose structural elements lacking the more preferred definition, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Even more preferred in accordance with the invention are the compoundsof the formula (If) in which each structural element is defined as givenabove as being even more preferred (“even more preferably”). For thosestructural elements lacking the even more preferred definition, thedefinition given above as being more preferred (“more preferably”) shallapply with the proviso that for those structural elements lacking themore preferred definition as well, the definition given above as beingespecially preferred (“especially preferably”) shall apply with theproviso that for those structural elements lacking the especiallypreferred definition as well, the definition in the summary of theinvention shall apply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (If) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being more preferred(“more preferably”) shall apply with the proviso that for thosestructural elements lacking the more preferred definition as well, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Alternatively, even more preferred in accordance with the invention arethe compounds of the formula (If) in which each structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (If) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Especially preferred in accordance with the invention are the compoundsof the formula (If) in which each structural element is defined as givenabove as being especially preferred (especially preferably). For thosestructural elements lacking the especially preferred definition, thedefinition in the summary of the invention shall apply.

Likewise especially preferred in accordance with the invention are thecompounds of the formula (If) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being especially preferred (especiallypreferably). For those structural elements lacking the especiallypreferred definition, the definition in the summary of the inventionshall apply.

With regard to compounds of formula (Ia-1) as defined above, thefollowing applies:

Preferred in accordance with the invention are the compounds of theformula (Ia-1) in which each structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

Likewise preferred in accordance with the invention are the compounds ofthe formula (Ia-1) in which Q is selected from the group consisting of(U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and (U-105) to(U-123) and in which each further structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

More preferred in accordance with the invention are the compounds of theformula (Ia-1) in which each structural element is defined as givenabove as being more preferred (“more preferably”). For those structuralelements lacking the more preferred definition, the definition givenabove as being especially preferred (“especially preferably”) shallapply with the proviso that for those structural elements lacking theespecially preferred definition as well, the definition in the summaryof the invention shall apply.

Likewise more preferred in accordance with the invention are thecompounds of the formula (Ia-1) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being more preferred (“more preferably”). Forthose structural elements lacking the more preferred definition, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Even more preferred in accordance with the invention are the compoundsof the formula (Ia-1) in which each structural element is defined asgiven above as being even more preferred (“even more preferably”).

For those structural elements lacking the even more preferreddefinition, the definition given above as being more preferred (“morepreferably”) shall apply with the proviso that for those structuralelements lacking the more preferred definition as well, the definitiongiven above as being especially preferred (“especially preferably”)shall apply with the proviso that for those structural elements lackingthe especially preferred definition as well, the definition in thesummary of the invention shall apply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Ia-1) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being more preferred(“more preferably”) shall apply with the proviso that for thosestructural elements lacking the more preferred definition as well, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Alternatively, even more preferred in accordance with the invention arethe compounds of the formula (Ia-1) in which each structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Ia-1) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Especially preferred in accordance with the invention are the compoundsof the formula (Ia-1) in which each structural element is defined asgiven above as being especially preferred (especially preferably). Forthose structural elements lacking the especially preferred definition,the definition in the summary of the invention shall apply.

Likewise especially preferred in accordance with the invention are thecompounds of the formula (Ia-1) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being especially preferred (especiallypreferably). For those structural elements lacking the especiallypreferred definition, the definition in the summary of the inventionshall apply.

With regard to compounds of formula (Ib-1) as defined above, thefollowing applies:

Preferred in accordance with the invention are the compounds of theformula (Ib-1) in which each structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

Likewise preferred in accordance with the invention are the compounds ofthe formula (Ib-1) in which Q is selected from the group consisting of(U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and (U-105) to(U-123) and in which each further structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

More preferred in accordance with the invention are the compounds of theformula (Ib-1) in which each structural element is defined as givenabove as being more preferred (“more preferably”). For those structuralelements lacking the more preferred definition, the definition givenabove as being especially preferred (“especially preferably”) shallapply with the proviso that for those structural elements lacking theespecially preferred definition as well, the definition in the summaryof the invention shall apply.

Likewise more preferred in accordance with the invention are thecompounds of the formula (Ib-1) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being more preferred (“more preferably”). Forthose structural elements lacking the more preferred definition, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Even more preferred in accordance with the invention are the compoundsof the formula (Ib-1) in which each structural element is defined asgiven above as being even more preferred (“even more preferably”). Forthose structural elements lacking the even more preferred definition,the definition given above as being more preferred (“more preferably”)shall apply with the proviso that for those structural elements lackingthe more preferred definition as well, the definition given above asbeing especially preferred (“especially preferably”) shall apply withthe proviso that for those structural elements lacking the especiallypreferred definition as well, the definition in the summary of theinvention shall apply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Ib-1) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being more preferred(“more preferably”) shall apply with the proviso that for thosestructural elements lacking the more preferred definition as well, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Alternatively, even more preferred in accordance with the invention arethe compounds of the formula (Ib-1) in which each structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (Ib-1) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Especially preferred in accordance with the invention are the compoundsof the formula (Ib-1) in which each structural element is defined asgiven above as being especially preferred (especially preferably). Forthose structural elements lacking the especially preferred definition,the definition in the summary of the invention shall apply.

Likewise especially preferred in accordance with the invention are thecompounds of the formula (Ib-1) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being especially preferred (especiallypreferably). For those structural elements lacking the especiallypreferred definition, the definition in the summary of the inventionshall apply.

With regard to compounds of formula (If-1) as defined above, thefollowing applies:

Preferred in accordance with the invention are the compounds of theformula (If-1) in which each structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

Likewise preferred in accordance with the invention are the compounds ofthe formula (If-1) in which Q is selected from the group consisting of(U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and (U-105) to(U-123) and in which each further structural element is defined as givenabove as being preferred (“preferably”). For those structural elementslacking the preferred definition, the definition in the summary of theinvention shall apply.

More preferred in accordance with the invention are the compounds of theformula (If-1) in which each structural element is defined as givenabove as being more preferred (“more preferably”). For those structuralelements lacking the more preferred definition, the definition givenabove as being especially preferred (“especially preferably”) shallapply with the proviso that for those structural elements lacking theespecially preferred definition as well, the definition in the summaryof the invention shall apply.

Likewise more preferred in accordance with the invention are thecompounds of the formula (If-1) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being more preferred (“more preferably”). Forthose structural elements lacking the more preferred definition, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Even more preferred in accordance with the invention are the compoundsof the formula (If-1) in which each structural element is defined asgiven above as being even more preferred (“even more preferably”). Forthose structural elements lacking the even more preferred definition,the definition given above as being more preferred (“more preferably”)shall apply with the proviso that for those structural elements lackingthe more preferred definition as well, the definition given above asbeing especially preferred (“especially preferably”) shall apply withthe proviso that for those structural elements lacking the especiallypreferred definition as well, the definition in the summary of theinvention shall apply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (If-1) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being more preferred(“more preferably”) shall apply with the proviso that for thosestructural elements lacking the more preferred definition as well, thedefinition given above as being especially preferred (“especiallypreferably”) shall apply with the proviso that for those structuralelements lacking the especially preferred definition as well, thedefinition in the summary of the invention shall apply.

Alternatively, even more preferred in accordance with the invention arethe compounds of the formula (If-1) in which each structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Likewise even more preferred in accordance with the invention are thecompounds of the formula (If-1) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being even more preferred (“even morepreferably”). For those structural elements lacking the even morepreferred definition, the definition given above as being especiallypreferred (“especially preferably”) shall apply with the proviso thatfor those structural elements lacking the especially preferreddefinition as well, the definition in the summary of the invention shallapply.

Especially preferred in accordance with the invention are the compoundsof the formula (If-1) in which each structural element is defined asgiven above as being especially preferred (especially preferably). Forthose structural elements lacking the especially preferred definition,the definition in the summary of the invention shall apply.

Likewise especially preferred in accordance with the invention are thecompounds of the formula (If-1) in which Q is selected from the groupconsisting of (U-1) to (U-61), (U-81) to (U-87), (U-89) to (U-103) and(U-105) to (U-123) and in which each further structural element isdefined as given above as being especially preferred (especiallypreferably). For those structural elements lacking the especiallypreferred definition, the definition in the summary of the inventionshall apply.

Saturated or unsaturated hydrocarbon radicals such as alkyl, alkanediylor alkenyl may in each case, both alone and in conjunction withheteroatoms, as in alkoxy, for example, be—where possible—eitherstraight-chain or branched.

Any substituted radicals may, unless indicated otherwise, be substitutedone or more times, and the substituents in the case of multiplesubstitutions may be alike or different.

In the definitions of radicals that are stated as being preferred,halogen (halo) is fluoro, chloro, bromo and iodo, very preferablyfluoro, chloro and bromo, and especially preferably fluoro and chloro.

Further specific embodiments of the invention are described hereafter:

A specific embodiment of the invention are the compounds of the formula(Ia) in which

Z is O;

X is O;

Q is selected from the group consisting of cyclopropyl and (U-1);

each m is independently 0 or 2;

R¹, R², R³, R⁴, R^(4a), R⁵, R^(5a), R⁶, R^(6a), R⁷, R^(7a), R⁸, R^(8a),R⁹, R^(9a), R¹⁰, R¹¹, R^(11a), R¹², R¹³, R¹⁴, R¹⁵, R^(v) and r are asdefined as preferred (“preferably”) in embodiment 1.

A specific embodiment of the invention are the compounds of the formula(Ia) in which

Z is O;

X is O;

Q is selected from the group consisting of cyclopropyl and (U-1);

each m is independently 0 or 2;

R¹, R², R³, R⁴, R⁷, R⁸, R⁹, R¹¹, R¹², R^(v) and r are as defined asbeing more preferred (“more preferably”) in embodiment 1.

A specific embodiment of the invention are the compounds of the formula(Ia) in which

Z is O;

Q is selected from the group consisting of cyclopropyl and (U-1);

R¹, R², R³, R⁴, R^(v) and r are as defined as being especially preferred(“especially preferably”) in embodiment 1.

A specific embodiment of the invention are the compounds of the formula(Ia) in which

Z is O;

X is O;

Q is selected from the group consisting of cyclopropyl and (U-1);

each m is independently 0 or 2;

R^(v) is chlor or methoxy;

r is 1 or 2;

R¹, R², R³, R⁴, R^(4a), R⁵, R^(5a), R⁶, R^(6a), R⁷, R^(7a), R⁸, R^(8a),R⁹, R^(9a), R¹⁰, R¹¹, R^(11a), R¹², R¹³, R¹⁴ and R¹⁵ are as defined aspreferred (“preferably”) in embodiment 1.

A specific embodiment of the invention are the compounds of the formula(Ia) in which

Z is O;

X is O;

Q is selected from the group consisting of cyclopropyl and (U-1);

each m is independently 0 or 2;

R^(v) is chlor or methoxy;

r is 1 or 2;

R¹, R², R³, R⁴, R⁷, R⁸, R⁹, R¹¹ and R¹² are as defined as being morepreferred (“more preferably”) in embodiment 1.

A specific embodiment of the invention are the compounds of the formula(Ia) in which

Z is O;

Q is selected from the group consisting of cyclopropyl and (U-1);

R^(v) is chlor or methoxy;

r is 1 or 2;

R¹, R², R³ and R⁴ are as defined as being especially preferred(“especially preferably”) in embodiment 1.

A specific embodiment of the invention are the compounds of the formula(Ib) in which

Z is O;

X is O;

Q is selected from the group consisting of methyl, ethyl, cyclopropyland (U-1);

each m is independently 0 or 2;

R¹, R², R³, R⁴, R^(4a), R⁵, R^(5a), R⁶, R^(6a), R⁷, R^(7a), R⁸, R^(8a),R⁹, R^(9a), R¹⁰, R¹¹, R^(11a), R¹², R¹³, R¹⁴, R¹⁵, R and r are asdefined as preferred (“preferably”) in embodiment 2.

A specific embodiment of the invention are the compounds of the formula(Ib) in which

Z is O;

X is O;

Q is selected from the group consisting of methyl, ethyl, cyclopropyland (U-1);

each m is independently 0 or 2;

R¹, R², R³, R⁴, R⁷, R⁸, R⁹, R¹¹, R¹², R^(v) and r are as defined asbeing more preferred (“more preferably”) in embodiment 2.

A specific embodiment of the invention are the compounds of the formula(Ib) in which

Z is O;

Q is selected from the group consisting of methyl, ethyl, cyclopropyland (U-1);

R¹, R², R³, R⁴, R and r are as defined as being especially preferred(“especially preferably”) in embodiment 2.

A specific embodiment of the invention are the compounds of the formula(Ib) in which

Z is O;

X is O;

Q is selected from the group consisting of methyl, ethyl, cyclopropyland (U-1);

each m is independently 0 or 2;

R^(v) is fluor, chlor or methoxy;

r is 1 or 2;

R¹, R², R³, R⁴, R^(4a), R⁵, R^(5a), R⁶, R^(6a), R⁷, R^(7a), R⁸, R^(8a),R⁹, R^(9a), R¹⁰, R¹¹, R^(11a), R¹², R¹³, R¹⁴ and R¹⁵ are as defined aspreferred (“preferably”) in embodiment 2.

A specific embodiment of the invention are the compounds of the formula(Ib) in which

Z is O;

X is O;

Q is selected from the group consisting of methyl, ethyl, cyclopropyland (U-1);

each m is independently 0 or 2;

R^(v) is fluor, chlor or methoxy;

r is 1 or 2;

R¹, R², R³, R⁴, R⁷, R⁸, R⁹, R¹¹ and R¹² are as defined as being morepreferred (“more preferably”) in embodiment 2.

A specific embodiment of the invention are the compounds of the formula(Ib) in which

Z is O;

Q is selected from the group consisting of methyl, ethyl, cyclopropyland (U-1);

R^(v) is fluor, chlor or methoxy;

r is 1 or 2;

R¹, R², R³ and R⁴ are as defined as being especially preferred(“especially preferably”) in embodiment 2. Aspecific embodiment of theinvention are the compounds of the formula (If) in which

Z is O;

X is O;

Q is selected from the group consisting of methyl, ethyl, cyclopropyl,(U-1), (U-49) and (U-103);

each m is independently 0 or 2;

R¹, R², R³, R⁴, R^(4a), R⁵, R^(5a), R⁶, R^(6a), R⁷, R^(7a), R⁸, R^(8a),R⁹, R^(9a), R¹⁰, R¹¹, R^(11a), R¹², R¹³, R¹⁴, R¹⁵, R and r are asdefined as preferred (“preferably”) in embodiment 6.

A specific embodiment of the invention are the compounds of the formula(If) in which

Z is O;

X is O;

Q is selected from the group consisting of methyl, ethyl, cyclopropyl,(U-1), (U-49) and (U-103);

each m is independently 0 or 2;

R¹, R², R³, R⁴, R⁷, R⁸, R⁹, R¹¹, R¹², R^(v) and r are as defined asbeing more preferred (“more preferably”) in embodiment 6.

A specific embodiment of the invention are the compounds of the formula(If) in which

Z is O;

Q is selected from the group consisting of methyl, ethyl, cyclopropyl,(U-1), (U-49) and (U-103);

R¹, R², R³, R⁴, R^(v) and r are as defined as being especially preferred(“especially preferably”) in embodiment 6.

A specific embodiment of the invention are the compounds of the formula(If) in which

Z is O;

X is O;

Q is selected from the group consisting of methyl, ethyl, cyclopropyl,(U-1), (U-49) and (U-103);

each m is independently 0 or 2;

R^(v) is fluor, chlor, methoxy, trifluoromethoxy, methyl ortrifluoromethyl;

r is 1, 2 or 3;

R¹, R², R³, R⁴, R^(4a), R⁵, R^(5a), R⁶, R^(6a), R⁷, R^(7a), R⁸, R^(8a),R⁹, R^(9a), R¹⁰, R¹¹, R^(11a), R¹², R¹³, R¹⁴ and R¹⁵ are as defined aspreferred (“preferably”) in embodiment 6.

A specific embodiment of the invention are the compounds of the formula(If) in which

Z is O;

X is O;

Q is selected from the group consisting of methyl, ethyl, cyclopropyl,(U-1), (U-49) and (U-103);

each m is independently 0 or 2;

R^(v) is fluor, chlor, methoxy, trifluoromethoxy, methyl ortrifluoromethyl;

r is 1, 2 or 3;

R¹, R², R³, R⁴, R⁷, R⁸, R⁹, R¹¹ and R¹² are as defined as being morepreferred (“more preferably”) in embodiment 6.

A specific embodiment of the invention are the compounds of the formula(If) in which

Z is O;

Q is selected from the group consisting of methyl, ethyl, cyclopropyl,(U-1), (U-49) and (U-103);

R^(v) is fluor, chlor, methoxy, trifluoromethoxy, methyl ortrifluoromethyl;

r is 1, 2 or 3;

R¹, R², R³ and R⁴ are as defined as being especially preferred(“especially preferably”) in embodiment 6.

Procedures and Methods

One or more of the following methods and variations as described inSchemes 1-8 can be used to prepare the compounds of formula (I). Thedefinitions of Z, Q, n, R¹, R² and R³ in the compounds of formulae (IA),(IB), (IC) and (II)-(XIII) below are as defined above in the Summary ofthe Invention unless otherwise noted. Formulae (IA)-(IC) are varioussubsets of formula (I), and all substituents for formulae (IA)-(IC) areas defined above for formula (I) unless otherwise noted. Roomtemperature is between about 20 and 25° C.

Compounds of formula (IA) (i.e. formula (I) wherein Z is oxygen and R³is H) can be prepared by the reaction of carboxylic acids of formula(II) with aryl or heteroaryl sulfonamides of formula (IIIA) as shown inScheme 1. Typically, an amide coupling reagent and a catalyst such asN,N-dimethylaminopyridine (DMAP) are used in the method of Scheme 1.Amide coupling reagents include1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC),N,N′-dicyclohexylcarbodiimide (DCC) and 1,1′-carbonyldiimidazole (CDI).The reaction can be carried out at temperatures ranging from roomtemperature to the reflux temperature of the solvent. Typical solventsinclude alcohols, ethers, esters, amides and halogenated hydrocarbons.Synthesis Example 1 describes a particularly useful set of conditionsutilizing EDC/DMAP in dichloromethane.

Compounds of formula (IA) can also be prepared by the reaction ofcarboxylic acid chlorides of formula (IV) with aryl or heteroarylsulfonamides of formula (IIIA) as shown in Scheme 2. The reactiontypically involves use of a base such as triethylamine or pyridine andoptionally a catalyst such as DMAP in the presence of a solvent. Thereaction can be carried out at temperatures ranging from roomtemperature to the reflux temperature of the solvent. Typical solventsinclude ethers, esters and halogenated hydrocarbons.

Compounds of formula (IB) wherein R³ is optionally substituted alkyl,alkenyl, alkynyl or cycloalkylalkyl and Z is oxygen can be prepared bythe reaction of compounds of formula (IA) with appropriately substitutedalkyl, alkenyl, alkynyl or cycloalkylalkyl halides and base as shown inScheme 3. Typical reaction conditions comprise potassium carbonate asthe base and DMF as the solvent.

Compounds of formula (IB) wherein R³ is C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,S(O)₂R⁹ or S(O)₂NR¹¹R¹² can be prepared by the reaction of compounds offormula (IA) with acyl or sulfonyl halides (e.g., Cl—C(X)R⁷, Cl—C(O)OR⁸,Cl—C(O)NR¹¹R¹², Cl—S(O)₂R⁹ or Cl—S(O)₂NR¹¹R¹²) by acylation orsulfonylation methods well known in the art.

Compounds of formula (IB) wherein R³ is optionally substituted alkyl,alkenyl, alkynyl, cycloalkyl or phenyl can be prepared by the reactionof acid chlorides of formula (IV) with sulfonamides of formula (IIIB) asshown in Scheme 4. Alternatively, compounds of formula (IB) wherein R³is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or phenylcan be prepared by the reaction of carboxylic acids of formula (II) withsulfonamides of formula (IIIB) by the method of Scheme 1.

Thioamides of formula (IC) (i.e. formula (I) wherein Z is sulfur) can beprepared by the reaction of compounds of formula (IA) or (IB) (i.e.formula (I) wherein Z is oxygen) with thiation reagents such asphosphorus pentasulfide or Lawesson's reagent as depicted in Scheme 5.

Compounds of formula (IIB) (i.e. formula (II) wherein R² is bromine) canbe prepared by the reaction of compounds of formula (IIA) (i.e. formula(II) wherein R² is H) with 1,2-dibromotetrachloroethane intetrahydrofurane in the presence of n-butyl-Li as described in WO2009/023179.

Compounds of formula (II) wherein R² is cyano can be prepared byreaction of compounds of formula (IIB) with CuCN by methods known in theart. Compounds of formula (II) wherein R² is nitro can be prepared byreaction of compounds of formula (IIA) by methods known in the art withnitric acid/sulfuric acid (cf. Chinese Journal of Chemistry 25, 241-245(2007), WO 2009/023179). Compounds of formula (II) wherein R² is OR⁴,NR⁵R⁶ or SR⁹ can be prepared from compounds of formula (II) wherein R²is halogen by standard displacement reactions well known in the art (cf.WO 2009/023179). Compounds of formula (II) wherein R² is F can beprepared by methods known in the art (cf. WO 2002/008224).

Carboxylic acids of formula (II) and acid chlorides of Formula (IV) canbe prepared by the reactions shown in Scheme 7. Reaction of a suitablysubstituted pyridine of formula (V) with an aminating agent of formula(VI) at temperatures ranging from room temperature to the boilingtemperature of the solvent like methylene chloride or chloroform affordsthe N-amino-pyridinium salt of formula (VII) (see, for example,Chemistry,—A European Journal 1, 557-563 (1995)). Treatment of salt(VII) with acetylene dicarboxylic acid dialkyl ester an inert solventsuch as dimethylformamide in the presence of a base like potassiumcarbonate results in formation of diester (VIII) (cf. WO 2008/124153).Reaction of (VIII) with aqueous sulfuric acid affords the carboxylicacid (IIA). The carboxylic acid of formula (IIA) can be converted to theacid chloride of formula (IVA) by well-known conventional means such astreatment with thionyl chloride or oxalyl chloride with a catalyticamount of N,N-dimethylformamide (DMF) in moderately polar, aproticsolvents including dichloromethane, dichloroethane, toluene and ethylacetate. Intermediates of formula (VI) can be prepared by a variety ofwell-known synthetic methods (cf. Chemistry—A European Journal 1,557-563 (1995) and WO 2011/112186).

Examples for intermediates of formula (II) or (VIII) are in severalcases commercially available (“Comm. av.”) or can be prepared accordingto well-known procedures, for example as indicated in table 1.

TABLE 1 R¹ n R² alkyl intermediate remarks 6-Br 1 COOMe Me (VIII) Comm.av. 7-OMe 1 COOMe Me (VIII) Comm. av. 4-Br 1 COOMe Me (VIII) Comm. av.7-CF₃ 1 COOMe Me (VIII) Comm. av. 4-Me 1 H — (IIA) Comm. av. 5-Me 1 H —(IIA) Comm. av. 6-Me 1 H — (IIA) Comm. av. 7-Me 1 H — (IIA) Comm. av.6-Br 1 H — (IIA) Comm. av. 6-F 1 H — (IIA) Comm. av. 6-Cl 1 H — (IIA)Comm. av. 5-Br 1 H — (IIA) Comm. av. 5-F 1 H — (IIA) Comm. av. 5-Cl 1 H— (IIA) Comm. av. 7-Br 1 H — (IIA) Comm. av. 7-F 1 H — (IIA) Comm. av.4-F 1 H — (IIA) Comm. av. 4-Br 1 H — (IIA) Comm. av. 6-Me 1 Br — (IIB)Comm. av. 6-Br 1 Cl — (II) Comm. av. 5-CF₃ 1 H — (IIA) Comm. av. 4-Br,6-Br 2 H — (IIA) Comm. av. 4-Me, 6-Br 2 H — (IIA) Comm. av. 5-Br, 7-CF₃2 H — (IIA) Comm. av. 5-OMe, 7-CF₃ 2 H — (IIA) Comm. av. 5-Cl, 7-CF₃ 2Cl — (II) Comm. av.

Sulfonamides of formulae (IIIA) and (IIIB) are known in the chemicalliterature or are available commercially. As shown in Scheme 8,sulfonamides of formula (IIIA) are readily prepared from thecorresponding sulfonyl chlorides of formula (IX) by reaction withammonia, while sulfonamides of formula (IIIB) are readily prepared fromthe corresponding sulfonyl chlorides of formula (IX) by reaction withR³NH₂. The sulfonyl chloride intermediates are available commercially orcan be prepared by a large variety of methods known in the literature.Three of the most common methods of sulfonyl chloride preparation areshown in Scheme 8, including (a) direct chlorosulfonylation of aromaticand heteroaromatic systems with chlorosulfonic acid, (b) oxidation ofsulfides (for example with sodium hypochlorite) in the prescence ofhydrochloric acid, and (c) diazotization and chlorosulfonylation ofaromatic and heteroaromatic amines. These three methods are meant onlyto be illustrative; a large variety of other synthetic methods areavailable for the preparation of sulfonyl chlorides and sulfonamides.

Pyridines of general formula (V) or their salts with organic orinorganic acids like hydrochloric acid are known in the chemicalliterature or are available commercially.

The compound according to the present invention can be preparedaccording to the processes described above. It will nevertheless beunderstood that, on the basis of his general knowledge and of availablepublications, the skilled worker will be able to adapt this methodaccording to the specifics of each of the compounds, which it is desiredto synthesize.

Isomers

Depending on the nature of the substituents, the compounds of theformula (I) may be in the form of geometric and/or optically activeisomers or corresponding isomer mixtures in different compositions.These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. Accordingly, the inventionencompasses both pure stereoisomers and any mixture of these isomers.

Methods and Uses

The invention also relates to methods for controlling animal pests, inwhich compounds of the formula (I) are allowed to act on animal pestsand/or their habitat. The control of the animal pests is preferablyconducted in agriculture and forestry, and in material protection.Preferably excluded here from are methods for the surgical ortherapeutic treatment of the human or animal body and diagnostic methodscarried out on the human or animal body.

The invention furthermore relates to the use of the compounds of theformula (I) as pesticides, in particular crop protection agents.

In the context of the present application, the term “pesticide” in eachcase also always comprises the term “crop protection agent”.

The compounds of the formula (I), having good plant tolerance,favourable homeotherm toxicity and good environmental compatibility, aresuitable for protecting plants and plant organs against biotic andabiotic stressors, for increasing harvest yields, for improving thequality of the harvested material and for controlling animal pests,especially insects, arachnids, helminths, nematodes and molluscs, whichare encountered in agriculture, in horticulture, in animal husbandry, inaquatic cultures, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector. They can preferably be used as pesticides. They are activeagainst normally sensitive and resistant species and against all or somestages of development. The abovementioned pests include:

pests from the phylum of the Arthropoda, in particular from the class ofthe Arachnida, for example Acarus spp., for example Acarus siro, Aceriakuko, Aceria sheldoni, Aculops spp., Aculus spp., for example Aculusfockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychusviennensis, Argas spp., Boophilus spp., Brevipalpus spp., for exampleBrevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroidesspp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoidespteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychusspp., for example Eotetranychus hicoriae, Epitrimerus pyri,Eutetranychus spp., for example Eutetranychus banksi, Eriophyes spp.,for example Eriophyes pyri, Glycyphagus domesticus, Halotydeusdestructor, Hemitarsonemus spp., for example Hemitarsonemus latus(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectusspp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp.,Oligonychus spp., for example Oligonychus coniferarum, Oligonychusilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychuspratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp.,Ornithonyssus spp., Panonychus spp., for example Panonychus citri(=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi),Phyllocoptruta oleivora, Platytetranychus multidigituli,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemusspp., Steneotarsonemus spinki, Tarsonemus spp., for example Tarsonemusconfusus, Tarsonemus pallidus, Tetranychus spp., for example Tetranychuscanadensis, Tetranychus cinnabarinus, Tetranychus turkestani,Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasateslycopersici;

from the class of the Chilopoda, for example Geophilus spp., Scutigeraspp.;

from the order or the class of the Collembola, for example Onychiurusarmatus; Sminthurus viridis;

from the class of the Diplopoda, for example Blaniulus guttulatus;

from the class of the Insecta, for example from the order of theBlattodea, for example Blatta orientalis, Blattella asahinai, Blattellagermanica, Leucophaea maderae, Panchlora spp., Parcoblatta spp.,Periplaneta spp., for example Periplaneta americana, Periplanetaaustralasiae, Supella longipalpa; from the order of the Coleoptera, forexample Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp.,Agelastica alni, Agriotes spp., for example Agriotes linneatus, Agriotesmancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobiumpunctatum, Anoplophora spp., Anthonomus spp., for example Anthonomusgrandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., forexample Atomaria linearis, Attagenus spp., Baris caerulescens,Bruchidius obtectus, Bruchus spp., for example Bruchus pisorum, Bruchusrufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., forexample Ceutorrhynchus assimilis, Ceutorrhynchus quadridens,Ceutorrhynchus rapae, Chaetocnema spp., for example Chaetocnemaconfinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus,Conoderus spp., Cosmopolites spp., for example Cosmopolites sordidus,Costelytra zealandica, Ctenicera spp., Curculio spp., for exampleCurculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi,Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi,Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturusadspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp.,for example Diabrotica balteata, Diabrotica barberi, Diabroticaundecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata,Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocisspp., Dicladispa armigera, Diloboderus spp., Epilachna spp., for exampleEpilachna borealis, Epilachna varivestis, Epitrix spp., for exampleEpitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrixsubcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides,Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyxspp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomecessquamosus, Hypothenemus spp., for example Hypothenemus hampei,Hypothenemus obscurus, Hypothenemus pubescens, Lachnosternaconsanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp.,Lema spp., Leptinotarsa decemlineata, Leucoptera spp., for exampleLeucoptera coffeella, Lissorhoptrus oryzophilus, Lixus spp.,Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp.,Melanotus spp., for example Melanotus longulus oregonensis, Meligethesaeneus, Melolontha spp., for example Melolontha melolontha, Migdolusspp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Niptushololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagusoryzae, Otiorhynchus spp., for example Otiorhynchus cribricollis,Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchusrugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedoncochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp.,for example Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotretaramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp.,Prostephanus truncatus, Psylliodes spp., for example Psylliodes affinis,Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobiusventralis, Rhizopertha dominica, Sitophilus spp., for example Sitophilusgranarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais,Sphenophorus spp., Stegobium paniceum, Sternechus spp., for exampleSternechus paludatus, Symphyletes spp., Tanymecus spp., for exampleTanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebriomolitor, Tenebrioides mauretanicus, Tribolium spp., for exampleTribolium audax, Tribolium castaneum, Tribolium confusum, Trogodermaspp., Tychius spp., Xylotrechus spp., Zabrus spp., for example Zabrustenebrioides;

from the order of the Diptera, for example Aedes spp., for example Aedesaegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp.,for example Agromyza frontella, Agromyza parvicornis, Anastrepha spp.,Anopheles spp., for example Anopheles quadrimaculatus, Anophelesgambiae, Asphondylia spp., Bactrocera spp., for example Bactroceracucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus,Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata,Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis,Cochliomya spp., Contarinia spp., for example Contarinia johnsoni,Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi,Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga,Cricotopus sylvestris, Culex spp., for example Culex pipiens, Culexquinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacusoleae, Dasineura spp., for example Dasineura brassicae, Delia spp., forexample Delia antiqua, Delia coarctata, Delia florilega, Delia platura,Delia radicum, Dermatobia hominis, Drosophila spp., for exampleDrosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Fanniaspp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrelliaspp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp.,Liriomyza spp., for example Liriomyza brassicae, Liriomyza huidobrensis,Liriomyza sativae, Lucilia spp., for example Lucilia cuprina, Lutzomyiaspp., Mansonia spp., Musca spp., for example Musca domestica, Muscadomestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp.,Paralauterborniella subcincta, Pegomya spp., for example Pegomya betae,Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp.,Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletisspp., for example Rhagoletis cingulata, Rhagoletis completa, Rhagoletisfausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella,Sarcophaga spp., Simulium spp., for example Simulium meridionale,Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., for exampleTipula paludosa, Tipula simplex;

from the order of the Hemiptera, for example Acizzia acaciaebaileyanae,Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiponspp., for example Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp.,Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis,Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., forexample Amrasca bigutulla, Amrasca devastans, Anuraphis cardui,Aonidiella spp., for example Aonidiella aurantii, Aonidiella citrina,Aonidiella inornata, Aphanostigma piri, Aphis spp., for example Aphiscitricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines,Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni,Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphisviburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp.,Aspidiotus spp., for example Aspidiotus nerii, Atanus spp., Aulacorthumsolani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspismelaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicorynebrassicae, Cacopsylla spp., for example Cacopsylla pyricola, Calligyponamarginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae,Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis,Chlorita onukii, Chondracris rosea, Chromaphis juglandicola,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,for example Coccus hesperidum, Coccus longulus, Coccuspseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp.,Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri,Diaspis spp., Drosicha spp., Dysaphis spp., for example Dysaphisapiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp.,Empoasca spp., for example Empoasca abrupta, Empoasca fabae, Empoascamaligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., for exampleEriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneuraspp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisiaspp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana,Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis,Hyalopterus pruni, Icerya spp., for example Icerya purchasi, Idiocerusspp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., forexample Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., forexample Lepidosaphes ulmi, Lipaphis erysimi, Lycorma delicatula,Macrosiphum spp., for example Macrosiphum euphorbiae, Macrosiphum lilii,Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphissacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum,Monellia costalis, Monelliopsis pecanis, Myzus spp., for example Myzusascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzuspersicae, Myzus nicotianae, Nasonovia ribisnigri, Nephotettix spp., forexample Nephotettix cincticeps, Nephotettix nigropictus, Nilaparvatalugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis,Pachypsylla spp., Parabemisia myricae, Paratrioza spp., for exampleParatrioza cockerelli, Parlatoria spp., Pemphigus spp., for examplePemphigus bursarius, Pemphigus populivenae, Peregrinus maidis,Phenacoccus spp., for example Phenacoccus madeirensis, Phloeomyzuspasserinii, Phorodon humuli, Phylloxera spp., for example Phylloxeradevastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcusspp., for example Planococcus citri, Prosopidopsylla flava,Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcusspp., for example Pseudococcus calceolariae, Pseudococcus comstocki,Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni,Psyllopsis spp., Psylla spp., for example Psylla buxi, Psylla mali,Psylla pyri, Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., forexample Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis,Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp.,Rhopalosiphum spp., for example Rhopalosiphum maidis, Rhopalosiphumoxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetiaspp., for example Saissetia coffeae, Saissetia miranda, Saissetianeglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum,Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatellafurcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae,Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae,Tomaspis spp., Toxoptera spp., for example Toxoptera aurantii, Toxopteracitricidus, Trialeurodes vaporariorum, Trioza spp., for example Triozadiospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;

from the suborder of the Heteroptera, for example Anasa tristis,Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylommalivida, Cavelerius spp., Cimex spp., for example Cimex adjunctus, Cimexhemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp.,Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocorishewetti, Dysdercus spp., Euschistus spp., for example Euschistus heros,Euschistus servus, Euschistus tristigmus, Euschistus variolarius,Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horciasnobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossusoccidentalis, Leptoglossus phyllopus, Lygocoris spp., for exampleLygocoris pabulinus, Lygus spp., for example Lygus elisus, Lygushesperus, Lygus lineolaris, Macropes excavatus, Monalonion atratum,Nezara spp., for example Nezara viridula, Oebalus spp., Piesma quadrata,Piezodorus spp., for example Piezodorus guildinii, Psallus spp.,Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoriscastanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.;

from the order of the Hymenoptera, for example Acromyrmex spp., Athaliaspp., for example Athalia rosae, Atta spp., Diprion spp., for exampleDiprion similis, Hoplocampa spp., for example Hoplocampa cookei,Hoplocampa testudinea, Lasius spp., Linepithema humile, Monomoriumpharaonis, Sirex spp., Solenopsis invicta, Tapinoma spp., Urocerus spp.,Vespa spp., for example Vespa crabro, Xeris spp.; from the order of theIsopoda, for example Armadillidium vulgare, Oniscus asellus, Porcellioscaber; from the order of the Isoptera, for example Coptotermes spp.,for example Coptotermes formosanus, Cornitermes cumulans, Cryptotermesspp., Incisitermes spp., Microtermes obesi, Odontotermes spp.,Reticulitermes spp., for example Reticulitermes flavipes, Reticulitermeshesperus;

from the order of the Lepidoptera, for example Achroia grisella,Acronicta major, Adoxophyes spp., for example Adoxophyes orana, Aedialeucomelas, Agrotis spp., for example Agrotis segetum, Agrotis ipsilon,Alabama spp., for example Alabama argillacea, Amyelois transitella,Anarsia spp., Anticarsia spp., for example Anticarsia gemmatalis,Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrixthurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp.,Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposinaniponensis, Cheimatobia brumata, Chilo spp., for example Chiloplejadellus, Chilo suppressalis, Choristoneura spp., Clysia ambiguella,Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp.,Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., forexample Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphaniaspp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium,Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., for exampleEphestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyaspostvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctisspp., for example Euproctis chrysorrhoea, Euxoa spp., Feltia spp.,Galleria mellonella, Gracillaria spp., Grapholitha spp., for exampleGrapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpaspp., for example Helicoverpa armigera, Helicoverpa zea, Heliothis spp.,for example Heliothis virescens Hofmannophila pseudospretella,Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoriaflavofasciata, Laphygma spp., Leucinodes orbonalis, Leucoptera spp., forexample Leucoptera coffeella, Lithocolletis spp., for exampleLithocolletis blancardella, Lithophane antennata, Lobesia spp., forexample Lobesia botrana, Loxagrotis albicosta, Lymantria spp., forexample Lymantria dispar, Lyonetia spp., for example Lyonetia clerkella,Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitisleda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogoncloacellus, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp.,Ostrinia spp., for example Ostrinia nubilalis, Oulema melanopus, Oulemaoryzae, Panolis flammea, Parnara spp., Pectinophora spp., for examplePectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., forexample Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycterspp., for example Phyllonorycter blancardella, Phyllonoryctercrataegella, Pieris spp., for example Pieris rapae, Platynota stultana,Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutellamaculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletiaspp., for example Pseudaletia unipuncta, Pseudoplusia includens,Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., for exampleSchoenobius bipunctifer, Scirpophaga spp., for example Scirpophagainnotata, Scotia segetum, Sesamia spp., for example Sesamia inferens,Sparganothis spp., Spodoptera spp., for example Spodoptera eradiana,Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica,Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Teciasolanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella,Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusiaspp., for example Trichoplusia ni, Tryporyza incertulas, Tuta absoluta,Virachola spp.;

from the order of the Orthoptera or Saltatoria, for example Achetadomesticus, Dichroplus spp., Gryllotalpa spp., for example Gryllotalpagryllotalpa, Hieroglyphus spp., Locusta spp., for example Locustamigratoria, Melanoplus spp., for example Melanoplus devastator,Paratlanticus ussuriensis, Schistocerca gregaria;

from the order of the Phthiraptera, for example Damalinia spp.,Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxeravastatrix, Phthirus pubis, Trichodectes spp.;

from the order of the Psocoptera, for example Lepinotus spp., Liposcelisspp.;

from the order of the Siphonaptera, for example, Ceratophyllus spp.,Ctenocephalides spp., for example Ctenocephalides canis, Ctenocephalidesfelis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

from the order of the Thysanoptera, for example Anaphothrips obscurus,Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens,Frankliniella spp., for example Frankliniella fusca, Frankliniellaoccidentalis, Frankliniella schultzei, Frankliniella tritici,Frankliniella vaccinii, Frankliniella williamsi, Heliothrips spp.,Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp.,Taeniothrips cardamomi, Thrips spp., for example Thrips palmi, Thripstabaci;

from the order of the Zygentoma (=Thysanura), for example Ctenolepismaspp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;

from the class of the Symphyla, for example Scutigerella spp., forexample Scutigerella immaculata;

pests from the phylum of the Mollusca, for example from the class of theBivalvia, for example Dreissena spp.,

and also from the class of the Gastropoda, for example Arion spp., forexample Arion ater rufus, Biomphalaria spp., Bulinus spp., Derocerasspp., for example Deroceras laeve, Galba spp., Lymnaea spp., Oncomelaniaspp., Pomacea spp., Succinea spp.;

animal and human parasites from the phyla of the Platylminthes andNematoda, for example Aelurostrongylus spp., Amidostomum spp.,Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephalaspp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp.,Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp.,Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp.,Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilariaspp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobiusspp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsisspp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronemaspp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepisspp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylusspp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muelleriusspp., Necator spp., Nematodirus spp., Nippostrongylus spp.,Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Opisthorchis spp.,Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp.,Parafilaria spp., Paragonimus spp., Paramphistomum spp.,Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylusspp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilariaspp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamusspp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp.,Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylusspp., Trichuris spp., Uncinaria spp., Wuchereria spp.;

plant pests from the phylum of the Nematoda, i.e. phytoparasiticnematodes, in particular Aglenchus spp., for example Aglenchus agricola,Anguina spp., for example Anguina tritici, Aphelenchoides spp., forexample Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimusspp., for example Belonolaimus gracilis, Belonolaimus longicaudatus,Belonolaimus nortoni, Bursaphelenchus spp., for example Bursaphelenchuscocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus,Cacopaurus spp., for example Cacopaurus pestis, Criconemella spp., forexample Criconemella curvata, Criconemella onoensis, Criconemellaornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconemaxenoplax), Criconemoides spp., for example Criconemoides ferniae,Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., forexample Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., forexample Globodera pallida, Globodera rostochiensis, Helicotylenchusspp., for example Helicotylenchus dihystera, Hemicriconemoides spp.,Hemicycliophora spp., Heterodera spp., for example Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hoplolaimus spp., Longidorusspp., for example Longidorus africanus, Meloidogyne spp., for exampleMeloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla,Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp.,Paraphelenchus spp., Paratrichodorus spp., for example Paratrichodorusminor, Pratylenchus spp., for example Pratylenchus penetrans,Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulciusspp., Radopholus spp., for example Radopholus citrophilus, Radopholussimilis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp.,Subanguina spp., Trichodorus spp., for example Trichodorus obtusus,Trichodorus primitivus, Tylenchorhynchus spp., for exampleTylenchorhynchus annulatus, Tylenchulus spp., for example Tylenchulussemipenetrans, Xiphinema spp., for example Xiphinema index.

Furthermore, it is possible to control, from the subkingdom of theProtozoa, the order of the Coccidia, for example Eimeria spp.

Nematodes

In the present context, the term “nematodes” comprises all species ofthe phylum Nematoda and here in particular species acting as parasiteson plants or fungi (for example species of the order Aphelenchida,Meloidogyne, Tylenchida and others) or else on humans and animals (forexample species of the orders Trichinellida, Tylenchida, Rhabditina andSpirurida) and causing damage in or on these living organisms, and alsoother parasitic helminths.

A nematicide in crop protection, as described herein, is capable ofcontrolling nematodes.

The term “controlling nematodes” means killing the nematodes orpreventing or impeding their development or their growth or preventingor impeding their penetration into or their sucking on plant tissue.

Here, the efficacy of the compounds is determined by comparingmortalities, gall formation, cyst formation, nematode density per volumeof soil, nematode density per root, number of nematode eggs per soilvolume, mobility of the nematodes between a plant or plant part treatedwith the compound of the formula (I) or the treated soil and anuntreated plant or plant part or the untreated soil (100%). Preferably,the reduction achieved is 25-50% in comparison to an untreated plant,plant part or the untreated soil, particularly preferably 51-79% andvery particularly preferably the complete kill or the completeprevention of development and growth of the nematodes by a reduction of80 to 100%. The control of nematodes as described herein also comprisesthe control of proliferation of the nematodes (development of cystsand/or eggs). Compounds of the formula (I) can also be used to keep theplants or animals healthy, and they can be employed curatively,preventatively or systemically for the control of nematodes.

The person skilled in the art knows methods for determining mortalities,gall formation, cyst formation, nematode density per volume of soil,nematode density per root, number of nematode eggs per volume of soil,mobility of the nematodes.

The use of a compound of the formula (I) may keep the plant healthy andalso comprises a reduction of the damage caused by nematodes and anincrease of the harvest yield.

In the present context, the term “nematodes” refers to plant nematodeswhich comprise all nematodes which damage plants. Plant nematodescomprise phytoparasitic nematodes and soil-borne nematodes. Thephytoparasitic nematodes include ectoparasites such as Xiphinema spp.,Longidorus spp. and Trichodorus spp.; semiparasites such as Tylenchulusspp.; migratory endoparasites such as Pratylenchus spp., Radopholus spp.and Scutellonema spp.; non-migratory parasites such as Heterodera spp.,Globodera spp. and Meloidogyne spp., and also stem and leafendoparasites such as Ditylenchus spp., Aphelenchoides spp. andHirschmaniella spp. Particularly damaging root-parasitic soil nematodesare, for example, cyst-forming nematodes of the genera Heterodera orGlobodera, and/or root gall nematodes of the genus Meloidogyne. Damagingspecies of these genera are, for example, Meloidogyne incognita,Heterodera glycines (soya bean cyst nematode), Globodera pallida andGlobodera rostochiensis (yellow potato cyst nematode), these speciesbeing controlled effectively by the compounds described in the presenttext. However, the use of the compounds described in the present text isby no means restricted to these genera or species, but also extends inthe same manner to other nematodes.

The plant nematodes include, for example, Aglenchus agricola, Anguinatritici, Aphelenchoides arachidis, Aphelenchoides fragaria, and the stemand leaf endoparasites Aphelenchoides spp., Belonolaimus gracilis,Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchuscocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus undBursaphelenchus spp., Cacopaurus pestis, Criconemella curvata,Criconemella onoensis, Criconemella ornata, Criconemella rusium,Criconemella xenoplax (=Mesocriconema xenoplax) and Criconemella spp.,

Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum andCriconemoides spp., Ditylenchus destructor, Ditylenchus dipsaci,Ditylenchus myceliophagus and also the stem and leaf endoparasitesDitylenchus spp., Dolichodorus heterocephalus, Globodera pallida(=Heterodera pallida), Globodera rostochiensis (yellow potato cystnematode), Globodera solanacearum, Globodera tabacum, Globodera virginiaand the non-migratory cyst-forming parasites Globodera spp.,Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchuserythrine, Helicotylenchus multicinctus, Helicotylenchus nannus,Helicotylenchus pseudorobustus and Helicotylenchus spp.,Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora nudata,Hemicycliophora parvana, Heterodera avenae, Heterodera cruciferae,Heterodera glycines (soya bean cyst nematode), Heterodera oryzae,Heterodera schachtii, Heterodera zeae and the non-migratory cyst-formingparasites Heterodera spp., Hirschmaniella gracilis, Hirschmaniellaoryzae, Hirschmaniella spinicaudata and the stem and leaf endoparasitesHirschmaniella spp., Hoplolaimus aegyptii, Hoplolaimus californicus,Hoplolaimus columbus, Hoplolaimus galeatus, Hoplolaimus indicus,Hoplolaimus magnistylus, Hoplolaimus pararobustus, Longidorus africanus,Longidorus breviannulatus, Longidorus elongatus, Longidoruslaevicapitatus, Longidorus vineacola and the ectoparasites Longidorusspp., Meloidogyne acronea, Meloidogyne africana, Meloidogyne arenaria,Meloidogyne arenaria thamesi, Meloidogyne artiella, Meloidogynechitwoodi, Meloidogyne coffeicola, Meloidogyne ethiopica, Meloidogyneexigua, Meloidogyne fallax, Meloidogyne graminicola, Meloidogynegraminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyneincognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis,Meloidogyne minor, Meloidogyne naasi, Meloidogyne paranaensis,Meloidogyne thamesi and the non-migratory parasites Meloidogyne spp.,Meloinema spp., Nacobbus aberrans, Neotylenchus vigissi, Paraphelenchuspseudoparietinus, Paratrichodorus allius, Paratrichodorus lobatus,Paratrichodorus minor, Paratrichodorus nanus, Paratrichodorus porosus,Paratrichodorus teres and Paratrichodorus spp., Paratylenchus hamatus,Paratylenchus minutus, Paratylenchus projectus and Paratylenchus spp.,Pratylenchus agilis, Pratylenchus alleni, Pratylenchus andinus,Pratylenchus brachyurus, Pratylenchus cerealis, Pratylenchus coffeae,Pratylenchus crenatus, Pratylenchus delattrei, Pratylenchusgiibbicaudatus, Pratylenchus goodeyi, Pratylenchus hamatus, Pratylenchushexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchuspenetrans, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchusteres, Pratylenchus thornei, Pratylenchus vulnus, Pratylenchus zeae andthe migratory endoparasites Pratylenchus spp., Pseudohalenchus minutus,Psilenchus magnidens, Psilenchus tumidus, Punctodera chalcoensis,Quinisulcius acutus, Radopholus citrophilus, Radopholus similis, themigratory endoparasites Radopholus spp., Rotylenchulus borealis,Rotylenchulus parvus, Rotylenchulus reniformis and Rotylenchulus spp.,Rotylenchus laurentinus, Rotylenchus macrodoratus, Rotylenchus robustus,Rotylenchus uniformis and Rotylenchus spp., Scutellonema brachyurum,Scutellonema bradys, Scutellonema clathricaudatum and the migratoryendoparasites Scutellonema spp., Subanguina radiciola, Tetylenchusnicotianae, Trichodorus cylindricus, Trichodorus minor, Trichodorusprimitivus, Trichodorus proximus, Trichodorus similis, Trichodorussparsus and the ectoparasites Trichodorus spp., Tylenchorhynchus agri,Tylenchorhynchus brassicae, Tylenchorhynchus clarus, Tylenchorhynchusclaytoni, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis,Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchusvulgaris and Tylenchorhynchus spp., Tylenchulus semipenetrans and thesemiparasites Tylenchulus spp., Xiphinema americanum, Xiphinemabrevicolle, Xiphinema dimorphicaudatum, Xiphinema index and theectoparasites Xiphinema spp.

Nematodes for the control of which a compound of the formula (I) may beused include nematodes of the genus Meloidogyne such as the Southernroot-knot nematode (Meloidogyne incognita), the Javanese root-knotnematode (Meloidogyne javanica), the Northern root-knot nematode(Meloidogyne hapla) and the peanut root-knot nematode (Meloidogynearenaria); nematodes of the genus Ditylenchus such as the potato rotnematode (Ditylenchus destructor) and stem and bulb eelworm (Ditylenchusdipsaci); nematodes of the genus Pratylenchus such as the cobroot-lesion nematode (Pratylenchus penetrans), the chrysanthemumroot-lesion nematode (Pratylenchus fallax), the coffee root nematode(Pratylenchus coffeae), the tea root nematode (Pratylenchus loosi) andthe walnut root-lesion nematode (Pratylenchus vulnus); nematodes of thegenus Globodera such as the yellow potato cyst nematode (Globoderarostochiensis) and the white potato cyst nematode (Globodera pallida);nematodes of the genus Heterodera such as the soya bean cyst nematode(Heterodera glycines) and beet cyst eelworm (Heterodera schachtii);nematodes of the genus Aphelenchoides such as the rice white-tipnematode (Aphelenchoides besseyi), the chrysanthemum nematode(Aphelenchoides ritzemabosi) and the strawberry nematode (Aphelenchoidesfragariae); nematodes of the genus Aphelenchus such as the fungivorousnematode (Aphelenchus avenae); nematodes of the genus Radopholus, suchas the burrowing nematode (Radopholus similis); nematodes of the genusTylenchulus such as the citrus root nematode (Tylenchulussemipenetrans); nematodes of the genus Rotylenchulus such as thereniform nematode (Rotylenchulus reniformis); tree-dwelling nematodessuch as the pine wood nematode (Bursaphelenchus xylophilus) and the redring nematode (Bursaphelenchus cocophilus) and the like.

Plants for the protection of which a compound of the formula (I) can beused include plants such as cereals (for example rice, barley, wheat,rye, oats, maize and the like), beans (soya bean, aduki bean, bean,broadbean, peas, peanuts and the like), fruit trees/fruits (apples,citrus species, pears, grapevines, peaches, Japanese apricots, cherries,walnuts, almonds, bananas, strawberries and the like), vegetable species(cabbage, tomato, spinach, broccoli, lettuce, onions, spring onion,pepper and the like), root crops (carrot, potato, sweet potato, radish,lotus root, turnip and the like), plant for industrial raw materials(cotton, hemp, paper mulberry, mitsumata, rape, beet, hops, sugar cane,sugar beet, olive, rubber, palm trees, coffee, tobacco, tea and thelike), cucurbits (pumpkin, cucumber, water melon, melon and the like),meadow plants (cocksfoot, sorghum, timothy-grass, clover, alfalfa andthe like), lawn grasses (mascarene grass, bentgrass and the like), spiceplants etc. (lavender, rosemary, thyme, parsley, pepper, ginger and thelike) and flowers (chrysanthemums, rose, orchid and the like).

The compounds of the formula (I) are particularly suitable forcontrolling coffee nematodes, in particular Pratylenchus brachyurus,Pratylenchus coffeae, Meloidogyne exigua, Meloidogyne incognita,Meloidogyne coffeicola, Helicotylenchus spp. and also Meloidogyneparanaensis, Rotylenchus spp., Xiphinema spp., Tylenchorhynchus spp. andScutellonema spp.

The compounds of the formula (I) are particularly suitable forcontrolling potato nematodes, in particular Pratylenchus brachyurus,Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus penetrans,Pratylenchus coffeae, Ditylenchus dipsaci and of Pratylenchus alleni,Pratylenchus andinus, Pratylenchus cerealis, Pratylenchus crenatus,Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus,Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus,Belonolaimus longicaudatus, Trichodorus cylindricus, Trichodorusprimitivus, Trichodorus proximus, Trichodorus similis, Trichodorussparsus, Paratrichodorus minor, Paratrichodorus allius, Paratrichodorusnanus, Paratrichodorus teres, Meloidogyne arenaria, Meloidogyne fallax,Meloidogyne hapla, Meloidogyne thamesi, Meloidogyne incognita,Meloidogyne chitwoodi, Meloidogyne javanica, Nacobbus aberrans,Globodera rostochiensis, Globodera pallida, Ditylenchus destructor,Radopholus similis, Rotylenchulus reniformis, Neotylenchus vigissi,Paraphelenchus pseudoparietinus, Aphelenchoides fragariae and Meloinemaspp.

The compounds of the formula (I) are particularly suitable forcontrolling tomato nematodes, in particular Meloidogyne arenaria,Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita,Pratylenchus penetrans and also Pratylenchus brachyurus, Pratylenchuscoffeae, Pratylenchus scribneri, Pratylenchus vulnus, Paratrichodorusminor, Meloidogyne exigua, Nacobbus aberrans, Globodera solanacearum,Dolichodorus heterocephalus and Rotylenchulus reniformis.

The compounds of the formula (I) are particularly suitable forcontrolling cucumber plant nematodes, in particular Meloidogynearenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyneincognita, Rotylenchulus reniformis and Pratylenchus thornei.

The compounds of the formula (I) are particularly suitable forcontrolling cotton nematodes, in particular Belonolaimus longicaudatus,Meloidogyne incognita, Hoplolaimus columbus, Hoplolaimus galeatus andRotylenchulus reniformis.

The compounds of the formula (I) are particularly suitable forcontrolling maize nematodes, in particular Belonolaimus longicaudatus,Paratrichodorus minor and also Pratylenchus brachyurus, Pratylenchusdelattrei, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchuszeae, (Belonolaimus gracilis), Belonolaimus nortoni, Longidorusbreviannulatus, Meloidogyne arenaria, Meloidogyne arenaria thamesi,Meloidogyne graminis, Meloidogyne incognita, Meloidogyne incognitaacrita, Meloidogyne javanica, Meloidogyne naasi, Heterodera avenae,Heterodera oryzae, Heterodera zeae, Punctodera chalcoensis, Ditylenchusdipsaci, Hoplolaimus aegyptii, Hoplolaimus magnistylus, Hoplolaimusgaleatus, Hoplolaimus indicus, Helicotylenchus digonicus,Helicotylenchus dihystera, Helicotylenchus pseudorobustus, Xiphinemaamericanum, Dolichodorus heterocephalus, Criconemella ornata,Criconemella onoensis, Radopholus similis, Rotylenchulus borealis,Rotylenchulus parvus, Tylenchorhynchus agri, Tylenchorhynchus clarus,Tylenchorhynchus claytoni, Tylenchorhynchus maximus, Tylenchorhynchusnudus, Tylenchorhynchus vulgaris, Quinisulcius acutus, Paratylenchusminutus, Hemicycliophora parvana, Aglenchus agricola, Anguina tritici,Aphelenchoides arachidis, Scutellonema brachyurum and Subanguinaradiciola.

The compounds of the formula (I) are particularly suitable forcontrolling soya bean nematodes, in particular Pratylenchus brachyurus,Pratylenchus pratensis, Pratylenchus penetrans, Pratylenchus scribneri,Belonolaimus longicaudatus, Heterodera glycines, Hoplolaimus columbusand also Pratylenchus coffeae, Pratylenchus hexincisus, Pratylenchusneglectus, Pratylenchus crenatus, Pratylenchus alleni, Pratylenchusagilis, Pratylenchus zeae, Pratylenchus vulnus, (Belonolaimus gracilis),Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica,Meloidogyne hapla, Hoplolaimus columbus, Hoplolaimus galeatus andRotylenchulus reniformis.

The compounds of the formula (I) are particularly suitable forcontrolling tobacco nematodes, in particular Meloidogyne incognita,Meloidogyne javanica and also Pratylenchus brachyurus, Pratylenchuspratensis, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchusneglectus, Pratylenchus crenatus, Pratylenchus thornei, Pratylenchusvulnus, Pratylenchus zeae, Longidorus elongatu, Paratrichodorus lobatus,Trichodorus spp., Meloidogyne arenaria, Meloidogyne hapla, Globoderatabacum, Globodera solanacearum, Globodera virginiae, Ditylenchusdipsaci, Rotylenchus spp., Helicotylenchus spp., Xiphinema americanum,Criconemella spp., Rotylenchulus reniformis, Tylenchorhynchus claytoni,Paratylenchus spp. and Tetylenchus nicotianae.

The compounds of the formula (I) are particularly suitable forcontrolling citrus nematodes, in particular Pratylenchus coffeae andalso Pratylenchus brachyurus, Pratylenchus vulnus, Belonolaimuslongicaudatus, Paratrichodorus minor, Paratrichodorus porosus,Trichodorus, Meloidogyne incognita, Meloidogyne incognita acrita,Meloidogyne javanica, Rotylenchus macrodoratus, Xiphinema americanum,Xiphinema brevicolle, Xiphinema index, Criconemella spp.,Hemicriconemoides, Radopholus similis and Radopholus citrophilus,Hemicycliophora arenaria, Hemicycliophora nudata and Tylenchulussemipenetrans.

The compounds of the formula (I) are particularly suitable forcontrolling banana nematodes, in particular Pratylenchus coffeae,Radopholus similis and also Pratylenchus giibbicaudatus, Pratylenchusloosi, Meloidogyne spp., Helicotylenchus multicinctus, Helicotylenchusdihystera and Rotylenchulus spp.

The compounds of the formula (I) are particularly suitable forcontrolling pineapple nematodes, in particular Pratylenchus zeae,Pratylenchus pratensis, Pratylenchus brachyurus, Pratylenchus goodeyi.,Meloidogyne spp., Rotylenchulus reniformis and also Longidoruselongatus, Longidorus laevicapitatus, Trichodorus primitivus,Trichodorus minor, Heterodera spp., Ditylenchus myceliophagus,Hoplolaimus californicus, Hoplolaimus pararobustus, Hoplolaimus indicus,Helicotylenchus dihystera, Helicotylenchus nannus, Helicotylenchusmulticinctus, Helicotylenchus erythrine, Xiphinema dimorphicaudatum,Radopholus similis, Tylenchorhynchus digitatus, Tylenchorhynchusebriensis, Paratylenchus minutus, Scutellonema clathricaudatum,Scutellonema bradys, Psilenchus tumidus, Psilenchus magnidens,Pseudohalenchus minutus, Criconemoides ferniae, Criconemoides onoenseand Criconemoides ornatum.

The compounds of the formula (I) are particularly suitable forcontrolling grapevine nematodes, in particular Pratylenchus vulnus,Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica,Xiphinema americanum, Xiphinema index and also Pratylenchus pratensis,Pratylenchus scribneri, Pratylenchus neglectus, Pratylenchus brachyurus,Pratylenchus thornei and Tylenchulus semipenetrans.

The compounds of the formula (I) are particularly suitable forcontrolling nematodes in tree crops—pome fruit, in particularPratylenchus penetrans and also Pratylenchus vulnus, Longidoruselongatus, Meloidogyne incognita and Meloidogyne hapla.

The compounds of the formula (I) are particularly suitable forcontrolling nematodes in tree crops—stone fruit, in particularPratylenchus penetrans, Pratylenchus vulnus, Meloidogyne arenaria,Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita,Criconemella xenoplax and of Pratylenchus brachyurus, Pratylenchuscoffeae, Pratylenchus scribneri, Pratylenchus zeae, Belonolaimuslongicaudatus, Helicotylenchus dihystera, Xiphinema americanum,Criconemella curvata, Tylenchorhynchus claytoni, Paratylenchus hamatus,Paratylenchus projectus, Scutellonema brachyurum and Hoplolaimusgaleatus.

The compounds of the formula (I) are particularly suitable forcontrolling nematodes in tree crops, sugar cane and rice, in particularTrichodorus spp., Criconemella spp. and also Pratylenchus spp.,Paratrichodorus spp., Meloidogyne spp., Helicotylenchus spp.,Tylenchorhynchus spp., Aphelenchoides spp., Heterodera spp, Xiphinemaspp. and Cacopaurus pestis.

In the present context, the term “nematodes” also refers to nematodesdamaging humans or animals.

Specific nematode species harmful to humans or to animals are:

Trichinellida, for example: Trichuris spp., Capillaria spp.,Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinellaspp.;

from the order of the Tylenchida, for example: Micronema spp.,Strongyloides spp.;

from the order of the Rhabditida, for example: Strongylus spp.,Triodontophorus spp., Oesophagodontus spp., Trichonema spp.,Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp.,Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp.,Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp.,Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp.,Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muelleriusspp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp.,Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.,Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerusspp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp.,Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagiaspp., Teladorsagia spp., Marshallagia spp., Cooperia spp.,Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp.,Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.;

from the order of the Spirurida, for example: Oxyuris spp., Enterobiusspp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.;Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp.,Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp.,Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp.,Parabronema spp.;

Draschia spp., Dracunculus spp.; Stephanofilaria spp., Parafilaria spp.,Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugiaspp., Wuchereria spp., Onchocerca spp., Spirocerca spp.

Many known nematicides also act against other parasitic helminths andare therefore used for controlling worms—not necessarily belonging tothe group Nematoda—which are parasites in humans and animals. Thepresent invention also relates to the use of the compounds of theformula (I) as anthelmintic medicaments. The pathogenic endoparasitichelminths include Platyhelminthes (e.g. Monogenea, cestodes andtrematodes), Acanthocephala and Pentastoma. The following helminths maybe mentioned as being preferred:

Monogenea: e.g.: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.;

Cestodes: from the order of the Pseudophyllidea, for example:Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligulaspp., Bothridium spp., Diplogonoporus spp.;

from the order of the Cyclophyllida, for example: Mesocestoides spp.,Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomaspp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaeniaspp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp.,Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp.,Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp.,Joyeuxiella spp., Diplopylidium spp.;

Trematodes: from the class of the Digenea, for example: Diplostomumspp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp.,Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp.,Leucochloridium spp., Brachylaima spp., Echinostoma spp.,Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciolaspp., Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp.,Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoronspp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp.,Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimusspp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimusspp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchisspp., Metorchis spp., Heterophyes spp., Metagonimus spp.;Acanthocephala: from the order of the Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order of thePolymorphida, for example: Filicollis spp.; from the order of theMoniliformida, for example: Moniliformis spp.;

from the order of the Echinorhynchida, for example, Acanthocephalusspp., Echinorhynchus spp., Leptorhynchoides spp.;

Pentastoma: from the order of the Porocephalida, for example, Linguatulaspp.

In the veterinary field and in animal keeping, the administration of thecompounds of the formula (I) is carried out by methods generally knownin the art, directly or enterally, parenterally, dermally or nasally inthe form of suitable preparations. Administration can be carried outprophylactically or therapeutically.

The compounds of the formula (I) can optionally, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, asmicrobicides or gametocides, for example as fungicides, antimycotics,bactericides, viricides (including agents against viroids) or as agentsagainst MLO (mycoplasma-like organisms) and RLO (rickettsia-likeorganisms). If appropriate, they can also be used as intermediates orprecursors for the synthesis of other active compounds.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of the formula (I). In somecases, the use forms comprise further pesticides and/or adjuvants whichimprove action, such as penetrants, e.g. vegetable oils, for examplerapeseed oil, sunflower oil, mineral oils, for example paraffin oils,alkyl esters of vegetable fatty acids, for example rapeseed oil methylester or soya oil methyl ester, or alkanol alkoxylates and/or spreaders,for example alkylsiloxanes and/or salts, for example organic orinorganic ammonium or phosphonium salts, for example ammonium sulphateor diammonium hydrogenphosphate and/or retention promoters, for exampledioctyl sulphosuccinate or hydroxypropyl guar polymers and/orhumectants, for example glycerol and/or fertilizers, for exampleammonium-, potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further possibleformulation types are described, for example, by Crop Life Internationaland in Pesticide Specifications, Manual on development and use of FAOand WHO specifications for pesticides, FAO Plant Production andProtection Papers—173, prepared by the FAO/WHO Joint Meeting onPesticide Specifications, 2004, ISBN: 9251048576. The formulations, inaddition to one or more compounds of the formula (I), optionallycomprise further agrochemically active compounds.

These are preferably formulations or use forms which compriseauxiliaries, for example extenders, solvents, spontaneity promoters,carriers, emulsifiers, dispersants, frost protectants, biocides,thickeners and/or further auxiliaries, for example adjuvants. Anadjuvant in this context is a component which enhances the biologicaleffect of the formulation, without the component itself having anybiological effect. Examples of adjuvants are agents which promoteretention, spreading, attachment to the leaf surface or penetration.

These formulations are prepared in a known way, for example by mixingthe compounds of the formula (I) with auxiliaries such as, for example,extenders, solvents and/or solid carriers and/or other auxiliaries suchas, for example, surfactants. The formulations are prepared either insuitable facilities or else before or during application.

The auxiliaries used may be substances suitable for imparting specialproperties, such as certain physical, technical and/or biologicalproperties, to the formulation of the compounds of the formula (I), orto the use forms prepared from these formulations (for exampleready-to-use pesticides such as spray liquors or seed dressingproducts).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, and also water.

In principle, it is possible to use all suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatic or chlorinated aliphatichydrocarbons, such as chlorobenzene, chloroethylene or methylenechloride, aliphatic hydrocarbons, such as cyclohexane, paraffins,petroleum fractions, mineral and vegetable oils, alcohols, such asmethanol, ethanol, isopropanol, butanol or glycol and their ethers andesters, ketones such as acetone, methyl ethyl ketone, methyl isobutylketone or cyclohexanone, strongly polar solvents, such as dimethylsulphoxide, and also water.

In principle, it is possible to use all suitable carriers. Usefulcarriers include especially: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticmaterials such as finely divided silica, alumina and natural orsynthetic silicates, resins, waxes and/or solid fertilizers. Mixtures ofsuch carriers can likewise be used. Useful carriers for granulesinclude: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite, dolomite, and synthetic granules ofinorganic and organic meals, and also granules of organic material suchas sawdust, paper, coconut shells, corn cobs and tobacco stalks.

Liquefied gaseous extenders or solvents can also be used. Particularlysuitable extenders or carriers are those which are gaseous at ambienttemperature and under atmospheric pressure, for example aerosolpropellant gases, such as halohydrocarbons, and also butane, propane,nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam-formers, dispersants or wettingagents with ionic or nonionic properties, or mixtures of thesesurfactants, are salts of polyacrylic acid, salts of lignosulphonicacid, salts of phenolsulphonic acid or naphthalenesulphonic acid,polycondensates of ethylene oxide with fatty alcohols or with fattyacids or with fatty amines, with substituted phenols (preferablyalkylphenols or arylphenols), salts of sulphosuccinic esters, taurinederivatives (preferably alkyl taurates), phosphoric esters ofpolyethoxylated alcohols or phenols, fatty esters of polyols, andderivatives of the compounds containing sulphates, sulphonates andphosphates, for example alkylaryl polyglycol ethers, alkylsulphonates,alkyl sulphates, arylsulphonates, protein hydrolysates, lignosulphitewaste liquors and methylcellulose. The presence of a surfactant isadvantageous if one of the compounds of the formula (I) and/or one ofthe inert carriers is insoluble in water and when the application takesplace in water.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyes such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and nutrients andtrace nutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc as further auxiliaries in the formulations and theuse forms derived therefrom.

Additional components may be stabilizers, such as low-temperaturestabilizers, preservatives, antioxidants, light stabilizers or otheragents which improve chemical and/or physical stability. Foam formers orantifoams may also be present.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids may also be present as additional auxiliaries in theformulations and the use forms derived therefrom. Further possibleauxiliaries are mineral and vegetable oils.

Optionally, further auxiliaries may be present in the formulations andthe use forms derived therefrom. Examples of such additives includefragrances, protective colloids, binders, adhesives, thickeners,thixotropic agents, penetrants, retention promoters, stabilizers,sequestrants, complexing agents, humectants, spreaders. In general, thecompounds of the formula (I) can be combined with any solid or liquidadditive commonly used for formulation purposes.

Useful retention promoters include all those substances which reduce thedynamic surface tension, for example dioctyl sulphosuccinate, orincrease the viscoelasticity, for example hydroxypropylguar polymers.Suitable penetrants in the present context are all those substanceswhich are usually used for improving the penetration of agrochemicalactive compounds into plants. Penetrants are defined in this context bytheir ability to penetrate from the (generally aqueous) applicationliquor and/or from the spray coating into the cuticle of the plant andthereby increase the mobility of active compounds in the cuticle. Themethod described in the literature (Baur et al., 1997, Pesticide Science51, 131-152) can be used to determine this property. Examples includealcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecylethoxylate (12), fatty acid esters, for example rapeseed oil methylester or soya oil methyl ester, fatty amine alkoxylates, for exampletallowamine ethoxylate (15), or ammonium and/or phosphonium salts, forexample ammonium sulphate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001 and 98% byweight of the compound of the formula (I) or, with particularpreference, between 0.01% and 95% by weight of the compound of theformula (I), more preferably between 0.5% and 90% by weight of thecompound of the formula (I), based on the weight of the formulation.

The content of the compound of the formula (I) in the use forms preparedfrom the formulations (in particular pesticides) may vary within wideranges. The concentration of the compound of the formula (I) in the useforms is usually between 0.00000001 and 95% by weight of the compound ofthe formula (I), preferably between 0.00001 and 1% by weight, based onthe weight of the use form. The compounds are employed in a customarymanner appropriate for the use forms.

Mixtures

The compounds of the formula (I) may also be employed as a mixture withone or more suitable fungicides, bactericides, acaricides,molluscicides, nematicides, insecticides, microbiologicals, beneficialspecies, herbicides, fertilizers, bird repellents, phytotonics,sterilants, safeners, semiochemicals and/or plant growth regulators, inorder thus, for example, to broaden the spectrum of action, to prolongthe duration of action, to increase the rate of action, to preventrepulsion or prevent evolution of resistance. In addition, such activecompound combinations may improve plant growth and/or tolerance toabiotic factors, for example high or low temperatures, to drought or toelevated water content or soil salinity. It is also possible to improveflowering and fruiting performance, optimize germination capacity androot development, facilitate harvesting and improve yields, influencematuration, improve the quality and/or the nutritional value of theharvested products, prolong storage life and/or improve theprocessability of the harvested products.

Furthermore, the compounds of the formula (I) can be present in amixture with other active compounds or semiochemicals such asattractants and/or bird repellants and/or plant activators and/or growthregulators and/or fertilizers. Likewise, the compounds of the formula(I) can be used to improve plant properties such as, for example,growth, yield and quality of the harvested material.

In a particular embodiment according to the invention, the compounds ofthe formula (I) are present in formulations or the use forms preparedfrom these formulations in a mixture with further compounds, preferablythose as described below.

If one of the compounds mentioned below can occur in differenttautomeric forms, these forms are also included even if not explicitlymentioned in each case.

Insecticides/Acaricides/Nematicides

The active compounds identified here by their common names are known andare described, for example, in the pesticide handbook (“The PesticideManual” 16th Ed., British Crop Protection Council 2012) or can be foundon the Internet (e.g. http://www.alanwood.net/pesticides).

(1) Acetylcholinesterase (AChE) inhibitors, such as, for example,carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; ororganophosphates, for example acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos,chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos,demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate,dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur,fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos,isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate,isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos,monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos,pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel antagonists, such as, for example,cyclodiene-organochlorines, for example chlordane and endosulfan orphenylpyrazoles (fiproles), for example ethiprole and fipronil.

(3) Sodium channel modulators/voltage-gated sodium channel blockers suchas, for example, pyrethroids, e.g. acrinathrin, allethrin, d-cis-transallethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrins-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin,beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,zeta-cypermethrin, cyphenothrin [(1R)-trans-isomer], deltamethrin,empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin,fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox,imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans-isomer],prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen,tefluthrin, tetramethrin, tetramethrin [(1R)-isomer)], tralomethrin andtransfluthrin or DDT or methoxychlor.

(4) Nicotinergic acetylcholine receptor (nAChR) agonists, such as, forexample, neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine orsulfoxaflor.

(5) Allosteric activators of the nicotinergic acetylcholine receptor(nAChR) such as, for example, spinosyns, e.g. spinetoram and spinosad.

(6) Chloride channel activators, such as, for example,avermectins/milbemycins, for example abamectin, emamectin benzoate,lepimectin and milbemectin.

(7) Juvenile hormone imitators such as, for example, juvenile hormoneanalogues, e.g. hydroprene, kinoprene and methoprene or fenoxycarb orpyriproxyfen.

(8) Active compounds with unknown or nonspecific mechanisms of actionsuch as, for example,

alkyl halides, e.g. methyl bromide and other alkyl halides; orchloropicrine or sulphuryl fluoride or borax or tartar emetic.

(9) Selective antifeedants, for example pymetrozine or flonicamid.

(10) Mite growth inhibitors, for example clofentezine, hexythiazox anddiflovidazin or etoxazole.

(11) Microbial disruptors of the insect gut membrane, for exampleBacillus thuringiensis subspecies israelensis, Bacillus sphaericus,Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensissubspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, andBT plant proteins: CrylAb, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab,Cry3Bb, Cry34/35Ab1.

(12) Oxidative phosphorylation inhibitors, ATP disruptors such as, forexample, diafenthiuron or organotin compounds, for example azocyclotin,cyhexatin and fenbutatin oxide or propargite or tetradifon;

(13) Oxidative phosphorylation decouplers acting by interrupting the Hproton gradient such as, for example, chlorfenapyr, DNOC andsulfluramid.

(14) Nicotinergic acetylcholine receptor antagonists such as, forexample, bensultap, cartap hydrochloride, thiocylam, andthiosultap-sodium.

(15) Chitin biosynthesis inhibitors, type 0, such as, for example,bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,teflubenzuron and triflumuron.

(16) Chitin biosynthesis inhibitors, type 1, for example buprofezin.

(17) Moulting inhibitors (in particular for Diptera, i.e. dipterans)such as, for example, cyromazine.

(18) Ecdysone receptor agonists such as, for example, chromafenozide,halofenozide, methoxyfenozide and tebufenozide.

(19) Octopaminergic agonists such as, for example, amitraz.

(20) Complex-III electron transport inhibitors such as, for example,hydramethylnone or acequinocyl or fluacrypyrim.

(21) Complex-I electron transport inhibitors, for example from the groupof the METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen,pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-gated sodium channel blockers, for example indoxacarb ormetaflumizone.

(23) Inhibitors of acetyl-CoA carboxylase such as, for example, tetronicand tetramic acid derivatives, e.g. spirodiclofen, spiromesifen andspirotetramat.

(24) Complex-IV electron transport inhibitors such as, for example,phosphines, e.g. aluminium phosphide, calcium phosphide, phosphine andzinc phosphide or cyanide.

(25) Complex II electron transport inhibitors, such as, for example,cyenopyrafen and cyflumetofen.

(28) Ryanodine receptor effectors, such as, for example, diamides, e.g.chlorantraniliprole, cyantraniliprole and flubendiamide,

further active compounds such as, for example, afidopyropen,azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate,chinomethionat, cryolite,dicofol, diflovidazin, fluensulfone, flometoquin, flufenerim,flufenoxystrobin, flufiprole, fluopyram, flupyradifurone, fufenozide,heptafluthrin, imidaclothiz, iprodione, meperfluthrin, paichongding,pyflubumide, pyrifluquinazon, pyriminostrobin, tetramethylfluthrin andiodomethane; furthermore preparations based on Bacillus firmus (I-1582,BioNeem, Votivo), and also the following compounds:3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from WO2005/077934) and1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indol-3,4′-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone(known from WO2003/106457),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494),3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO2009/049851),3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonate(known from WO2009/049851),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160),4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known fromWO2003/076415), PF1364 (CAS Reg. No. 1204776-60-2),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}benzamide(known from WO2005/085216),4-{5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl}-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}-1-naphthamide(known from WO2009/002809), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO2005/085216), methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216),1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide(known from WO2010/069502),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from CN102057925),3-chloro-N-(2-cyanopropan-2-yl)-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]phthalamide(known from WO2012/034472),8-chloro-N-[(2-chloro-5-methoxyphenyl)sulphonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide(known from WO2010/129500),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamide(known from WO2009/080250),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamide(known from WO2012/029672),1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate(known from WO2009/099929),1-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate(known from WO2009/099929),(5S,8R)-1-[(6-chloropyridin-3-yl)methyl]-9-nitro-2,3,5,6,7,8-hexahydro-1H-5,8-epoxyimidazo[1,2-a]azepine(known from WO2010/069266),(2E)-1-[(6-chloropyridin-3-yl)methyl]-N′-nitro-2-pentylidenehydrazinecarboximidamide(known from WO2010/060231),4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine(known from CN101337940),N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(known from WO2008/134969).

Fungicides

The active compounds specified herein by their common name are known anddescribed, for example, in “Pesticide Manual” or on the Internet (forexample: http://www.alanwood.net/pesticides).

(1) Inhibitors of ergosterol biosynthesis such as, for example, (1.1)aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole,(1.5) cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8)diniconazole, (1.9) diniconazole-M, (1.10) dodemorph, (1.11) dodemorphacetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol,(1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18)fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21)flusilazole, (1.22) flutriafole, (1.23) furconazole, (1.24)furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalilsulphate, (1.28) imibenconazole, (1.29) ipconazole, (1.30) metconazole,(1.31) myclobutanil, (1.32) naftifin, (1.33) nuarimol, (1.34)oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37)penconazole, (1.38) piperalin, (1.39) prochloraz, (1.40) propiconazole,(1.41) prothioconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44)quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47)tebuconazole, (1.48) terbinafin, (1.49) tetraconazole, (1.50)triadimefon, (1.51) triadimenol, (1.52) tridemorph, (1.53) triflumizole,(1.54) triforine, (1.55) triticonazole, (1.56) uniconazole, (1.57)uniconazole-P, (1.58) viniconazole, (1.59) voriconazole, (1.60)1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61) methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,(1.62)N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide,(1.63)N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamideand (1.64)0-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazole-1-carbothioate,(1.65) pyrisoxazole.

(2) Respiration inhibitors (respiratory chain inhibitors) such as, forexample, (2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4)diflumetorim, (2.5) fenfuram, (2.6) fluopyram, (2.7) flutolanil, (2.8)fluxapyroxad, (2.9) furametpyr, (2.10) furmecyclox, (2.11) isopyrazammixture of the syn-epimeric racemate 1RS,4SR,9RS and the anti-empimericracemate 1RS,4SR,9SR, (2.12) isopyrazam (anti-epimeric racemate), (2.13)isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.14) isopyrazam(anti-epimeric enantiomer 1S,4R,9R), (2.15) isopyrazam (syn-epimericracemate 1RS,4SR,9RS), (2.16) isopyrazam (syn-epimeric enantiomer1R,4S,9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.18)mepronil, (2.19) oxycarboxin, (2.20) penflufen, (2.21) penthiopyrad,(2.22) sedaxane, (2.23) thifluzamide, (2.24)1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(2.25)3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,(2.26)3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide,(2.27)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.28)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxyJ}phenyl)ethyl]quinazoline-4-amine, (2.29) benzovindiflupyr, (2.30)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamideand (2.31)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.32)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.33)1,3,5-trimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.34)1-methyl-3-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.35)1-methyl-3-(trifluoromethyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.36)1-methyl-3-(trifluoromethyl)-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.37)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.38)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.39)1,3,5-trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.40)1,3,5-trimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.41) benodanil, (2.42)2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,(2.43) isofetamid

(3) Respiration inhibitors (respiratory chain inhibitors) acting oncomplex III of the respiratory chain such as, for example, (3.1)ametoctradin, (3.2) amisulbrom, (3.3) azoxystrobin, (3.4) cyazofamid,(3.5) coumethoxystrobin, (3.6) coumoxystrobin, (3.5) dimoxystrobin,(3.8) enestroburin, (3.9) famoxadone, (3.10) fenamidone, (3.11)flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxim-methyl, (3.14)metominostrobin, (3.15) orysastrobin, (3.16) picoxystrobin, (3.17)pyraclostrobin, (3.18) pyrametostrobin, (3.19) pyraoxystrobin, (3.20)pyribencarb, (3.21) triclopyricarb, (3.22) trifloxystrobin, (3.23)(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide,(3.24)(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide,(3.25)(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide,(3.26)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,(3.27)(2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,(3.28)2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,(3.29)5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,(3.30) methyl(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulphanyl)methyl]phenyl}-3-methoxyprop-2-enoate,(3.31)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,(3.32)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(4) inhibitors of mitosis and cell division such as, for example, (4.1)benomyl, (4.2) carbendazim, (4.3) chlorfenazole, (4.4) diethofencarb,(4.5) ethaboxam, (4.6) fluopicolid, (4.7) fuberidazole, (4.8)pencycuron, (4.9) thiabendazole, (4.10) thiophanate-methyl, (4.11)thiophanate, (4.12) zoxamide, (4.13)5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidineand (4.14)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.

(5) Compounds having multisite activity such as, for example, (5.1)Bordeaux mixture, (5.2) captafol, (5.3) captan, (5.4) chlorothalonil,(5.5) copper preparations such as copper hydroxide, (5.6) coppernaphthenate, (5.7) copper oxide, (5.8) copper oxychloride, (5.9) coppersulphate, (5.10) dichlofluanid, (5.11) dithianon, (5.12) dodine, (5.13)dodine free base, (5.14) ferbam, (5.15) fluorfolpet, (5.16) folpet,(5.17) guazatine, (5.18) guazatine acetate, (5.19) iminoctadine, (5.20)iminoctadine albesilate, (5.21) iminoctadine triacetate, (5.22)mancopper, (5.23) mancozeb, (5.24) maneb, (5.25) metiram, (5.26) zincmetiram, (5.27) copper-oxine, (5.28) propamidine, (5.29) propineb,(5.30) sulphur and sulphur preparations such as, for example calciumpolysulphide, (5.31) thiram, (5.32) tolylfluanid, (5.33) zineb, (5.34)ziram and (5.35) anilazine.

(6) Resistance inducers such as, for example, (6.1)acibenzolar-S-methyl, (6.2) isotianil, (6.3) probenazole, (6.4) tiadiniland (6.5) laminarin.

(7) Inhibitors of amino acid and protein biosynthesis such as, forexample, (7.1), (7.2) blasticidin-S, (7.3) cyprodinil, (7.4)kasugamycin, (7.5) kasugamycin hydrochloride hydrate, (7.6) mepanipyrim,(7.7) pyrimethanil, (7.8)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolineand (7.9) oxytetracycline and (7.10) streptomycin.

(8) ATP production inhibitors such as, for example, (8.1) fentinacetate, (8.2) fentin chloride, (8.3) fentin hydroxide and (8.4)silthiofam.

(9) Inhibitors of cell wall synthesis such as, for example, (9.1)benthiavalicarb, (9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb,(9.5) mandipropamid, (9.6) polyoxins, (9.7) polyoxorim, (9.8)validamycin A, (9.9) valifenalate and (9.10) polyoxin B.

(10) Inhibitors of lipid and membrane synthesis such as, for example,(10.1) biphenyl, (10.2) chlorneb, (10.3) dicloran, (10.4) edifenphos,(10.5) etridiazole, (10.6) iodocarb, (10.7) iprobenfos, (10.8)isoprothiolane, (10.9) propamocarb, (10.10) propamocarb hydrochloride,(10.11) prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14)tecnazene and (10.15) tolclofos-methyl.

(11) Melanin biosynthesis inhibitors, for example (11.1) carpropamid,(11.2) diclocymet, (11.3) fenoxanil, (11.4) fthalide, (11.5) pyroquilon,(11.6) tricyclazole and (11.7) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

(12) Inhibitors of nucleic acid synthesis such as, for example, (12.1)benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4)clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl,(12.8) hymexazole, (12.9) metalaxyl, (12.10) metalaxyl-M (mefenoxam),(12.11) ofurace, (12.12) oxadixyl, (12.13) oxolinic acid and (12.14)octhilinone.

(13) Signal transduction inhibitors such as, for example, (13.1)chlozolinate, (13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione,(13.5) procymidone, (13.6) quinoxyfen, (13.7) vinclozolin and (13.8)proquinazid.

(14) Decouplers such as, for example, (14.1) binapacryl, (14.2) dinocap,(14.3) ferimzone, (14.4) fluazinam and (14.5) meptyldinocap.

(15) Further compounds such as, for example, (15.1) benthiazole, (15.2)bethoxazine, (15.3) capsimycin, (15.4) carvone, (15.5) chinomethionat,(15.6) pyriofenone (chlazafenone), (15.7) cufraneb, (15.8) cyflufenamid,(15.9) cymoxanil, (15.10) cyprosulfamide, (15.11) dazomet, (15.12)debacarb, (15.13) dichlorophen, (15.14) diclomezine, (15.15)difenzoquat, (15.16) difenzoquat methylsulphate, (15.17) diphenylamine,(15.18) EcoMate, (15.19) fenpyrazamine, (15.20) flumetover, (15.21)fluorimid, (15.22) flusulfamide, (15.23) flutianil, (15.24)fosetyl-aluminium, (15.25) fosetyl-calcium, (15.26) fosetyl-sodium,(15.27) hexachlorobenzene, (15.28) irumamycin, (15.29) methasulfocarb,(15.30) methyl isothiocyanate, (15.31) metrafenone, (15.32) mildiomycin,(15.33) natamycin, (15.34) nickel dimethyldithiocarbamate, (15.35)nitrothal-isopropyl, (15.36) octhilinone, (15.37) oxamocarb, (15.38)oxyfenthiin, (15.39) pentachlorophenol and its salts, (15.40)phenothrin, (15.41) phosphoric acid and its salts, (15.42)propamocarb-fosetylate, (15.43) propanosine-sodium, (15.44) pyrimorph,(15.45)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(15.46)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(15.47) pyrrolnitrin, (15.48) tebufloquin, (15.49) tecloftalam, (15.50)tolnifanide, (15.51) triazoxide, (15.52) trichlamide, (15.53) zarilamid,(15.54)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (15.55)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.56)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.57)1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.58) 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl1H-imidazole-1-carboxylate, (15.59)2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine, (15.60)2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (15.61)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.62)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(15.63)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(15.64)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,(15.65) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.66)2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine,(15.67) 2-phenylphenol and salts, (15.68)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.69) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (15.70)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(15.71)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(15.72) 5-amino-1,3,4-thiadiazole-2-thiol, (15.73)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulphonohydrazide,(15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine, (15.75)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4-amine, (15.76)5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidine-7-amine, (15.77) ethyl(2Z)-3-amino-2-cyano-3-phenylacrylate, (15.78)N′-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(15.79)N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(15.80)N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(15.81)N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,(15.82)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,(15.83)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide,(15.84)N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(15.85)N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(15.86)N′-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide,(15.87)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide,(15.88)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,(15.89)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,(15.90) pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.91) phenazine-1-carboxylic acid, (15.92) quinolin-8-ol, (15.93)quinolin-8-ol sulphate (2:1), (15.94) tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.95)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.96)N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.97)N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.98)3-(difluoromethyl)-1-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.99)N-(2′,5′-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(15.100)3-(difluoromethyl)-1-methyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.101)5-fluoro-1,3-dimethyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.102) 2-chloro-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.103)3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.104)N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.105)3-(difluoromethyl)-N-(4′-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide,(15.106)N-(4′-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.107) 2-chloro-N-(4′-ethynylbiphenyl-2-yl)nicotinamide, (15.108)2-chloro-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.109)4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide,(15.110)5-fluoro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.111)2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.112)3-(difluoromethyl)-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.113)5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.114)2-chloro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.115)(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone,(15.116)N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulphonyl)valinamide,(15.117) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.118)but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.119) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.120) propyl3,4,5-trihydroxybenzoate, (15.121)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(15.122)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(15.123)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(15.124)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.125)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.126)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.127)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.128)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (15.129)5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(15.130)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.131)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.132)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.133)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (15.134)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (15.135)5-(allylsulphanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(15.136)5-(allylsulphanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(15.137)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.138)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.139)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.140)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.141)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.142)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.143)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.144)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.145)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(15.146) 2-(6-benzylpyridin-2-yl)quinazoline, (15.147)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.148)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.149) abscisic acid, (15.150)3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide,(15.151)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(15.152)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.153)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.154)N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.155)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.156)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.157)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.158)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.159)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.160)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.161)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.162)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.163)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.164)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.165)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.166)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.167)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.168)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.169)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.170)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.171)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.172)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(15.173)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.174)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.175)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.176)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carbothioamide,(15.177)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-H-pyrazole-4-carboxamide,(15.178)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-H-pyrazole-4-carboxamide,(15.179)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.180)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(15.181) N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenylJ}-N-ethyl-N-methylimidoformamide, (15.182)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine.All mixing components mentioned in classes (1) to (15) can, if they arecapable on the basis of their functional groups, optionally form saltswith suitable bases or acids.

Biological Pesticides as Mixing Components

The compounds of the formula (I) can be combined with biologicalpesticides.

Biological pesticides comprise in particular bacteria, fungi, yeasts,plant extracts and products formed by microorganisms, including proteinsand secondary metabolites.

Biological pesticides comprise bacteria such as spore-forming bacteria,root-colonising bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which are employed or can be used asbiological pesticides are:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, in particular B. cereus strain CNCM I-1562 or Bacillus firmus,strain I-1582 (Accession number CNCM I-1582) or Bacillus pumilus, inparticular strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, in particular strainGB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421) Bacillus thuringiensis, in particular B.thuringiensis subspecies israelensis (serotype H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, inparticular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Acession Number NRRL 30232).

Examples of fungi and yeasts which are employed or can be used asbiological pesticides are:

Beauveria bassiana, in particular strain ATCC 74040, Coniothyriumminitans, in particular strain CON/M/91-8 (Accession No. DSM-9660),Lecanicillium spp., in particular strain HRO LEC 12, Lecanicilliumlecanii, (formerly known as Verticillium lecanii), in particular strainKVO1, Metarhizium anisopliae, in particular strain F52 (DSM3884/ATCC90448), Metschnikowia fructicola, in particular strain NRRL Y-30752,Paecilomyces fumosoroseus (now: Isaria fumosorosea), in particularstrain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874),Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL89/030550), Talaromyces flavus, in particular strain V117b, Trichodermaatroviride, in particular strain SC1 (Accession Number CBS 122089),Trichoderma harzianum, in particular T. harzianum rifai T39. (AccessionNumber CNCM I-952).

Examples of viruses which are employed or can be used as biologicalpesticides are:

Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydiapomonella (codling moth) granulosis virus (GV), Helicoverpa armigera(cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua(beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health. Exampleswhich may be mentioned are:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particularBurkholderia cepacia (formerly known as Pseudomonas cepacia), Gigasporaspp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillusbuchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp.,Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp.,Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganismsincluding proteins and secondary metabolites which are employed or canbe used as biological pesticides are:

Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassianigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza,Fungastop, Heads Up (Chenopodium quinoa saponin extract),Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,“Requiem™ Insecticide”, rotenone, ryania/ryanodine, Symphytumofficinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulummajus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract, inparticular oilseed rape powder or mustard powder.

Safener as Mixing Components

The compounds of the formula (I) can be combined with safeners such as,for example, benoxacor, cloquintocet (-mexyl), cyometrinil,cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim,flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr(-diethyl), naphthalic anhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulphonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and plant parts can be treated in accordance with theinvention. Here, plants are to be understood to mean all plants andplant parts such as wanted and unwanted wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya bean, potato, sugarbeet, sugar cane, tomatoes, peas and other vegetable species, cotton,tobacco, oilseed rape, and also fruit plants (with the fruits apples,pears, citrus fruits and grapevines). Crop plants can be plants whichcan be obtained by conventional breeding and optimization methods or bybiotechnological and genetic engineering methods or combinations ofthese methods, including the transgenic plants and including the plantvarieties which can or cannot be protected by varietal property rights.Plant parts should be understood to mean all parts and organs of theplants above and below ground, such as shoot, leaf, flower and root,examples given being leaves, needles, stalks, stems, flowers, fruitbodies, fruits and seeds, and also tubers, roots and rhizomes. Parts ofplants also include harvested plants and vegetative and generativepropagation material, for example seedlings, tubers, rhizomes, cuttingsand seeds.

Treatment according to the invention of the plants and plant parts withthe compounds of the formula (I) is carried out directly or by allowingthe compounds to act on the surroundings, environment or storage spaceby the customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injection and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andalso parts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(genetically modified organisms), and parts thereof are treated. Theterm “parts” or “parts of plants” or “plant parts” has been explainedabove. The invention is used with particular preference to treat plantsof the respective commercially customary cultivars or those that are inuse. Plant cultivars are to be understood as meaning plants having newproperties (“traits”) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They can becultivars, varieties, bio- or genotypes.

Transgenic Plant, Seed Treatment and Integration Events

The transgenic plants or plant cultivars (those obtained by geneticengineering) which are to be treated with preference in accordance withthe invention include all plants which, through the geneticmodification, received genetic material which imparts particularadvantageous useful properties (“traits”) to these plants. Examples ofsuch properties are better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to levels of wateror soil salinity, enhanced flowering performance, easier harvesting,accelerated ripening, higher yields, higher quality and/or a highernutritional value of the harvested products, better storage life and/orprocessability of the harvested products. Further and particularlyemphasized examples of such properties are increased resistance of theplants against animal and microbial pests, such as against insects,arachnids, nematodes, mites, slugs and snails owing, for example, totoxins formed in the plants, in particular those formed in the plants bythe genetic material from Bacillus thuringiensis (for example by thegenes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9cCry2Ab, Cry3Bb and CryIF and also combinations thereof), furthermoreincreased resistance of the plants against phytopathogenic fungi,bacteria and/or viruses owing, for example, to systemic acquiredresistance (SAR), systemin, phytoalexins, elicitors and also resistancegenes and correspondingly expressed proteins and toxins, and alsoincreased tolerance of the plants to certain herbicidally activecompounds, for example imidazolinones, sulphonylureas, glyphosate orphosphinothricin (for example the “PAT” gene). The genes which impartthe desired traits in question may also be present in combinations withone another in the transgenic plants. Examples of transgenic plantswhich may be mentioned are the important crop plants, such as cereals(wheat, rice, triticale, barley, rye, oats), maize, soya beans,potatoes, sugar beet, sugar cane, tomatoes, peas and other types ofvegetable, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), with particularemphasis being given to maize, soya beans, wheat, rice, potatoes,cotton, sugar cane, tobacco and oilseed rape. Traits which areparticularly emphasized are the increased resistance of the plants toinsects, arachnids, nematodes and slugs and snails.

Crop Protection—Types of Treatment

The treatment of the plants and plant parts with the compounds of theformula (I) is carried out directly or by action on their surroundings,habitat or storage space using customary treatment methods, for exampleby dipping, spraying, atomizing, irrigating, evaporating, dusting,fogging, broadcasting, foaming, painting, spreading-on, injecting,watering (drenching), drip irrigating and, in the case of propagationmaterial, in particular in the case of seed, furthermore as a powder fordry seed treatment, a solution for liquid seed treatment, awater-soluble powder for slurry treatment, by incrusting, by coatingwith one or more coats, etc. It is furthermore possible to apply thecompounds of the formula (I) by the ultra-low volume method or to injectthe application form or the compound of the formula (I) itself into thesoil.

A preferred direct treatment of the plants is foliar application, i.e.the compounds of the formula (I) are applied to the foliage, wheretreatment frequency and the application rate should be adjustedaccording to the level of infestation with the pest in question.

In the case of systemically active compounds, the compounds of theformula (I) also access the plants via the root system. The plants arethen treated by the action of the compounds of the formula (I) on thehabitat of the plant. This may be done, for example, by drenching, or bymixing into the soil or the nutrient solution, i.e. the locus of theplant (e.g. soil or hydroponic systems) is impregnated with a liquidform of the compounds of the formula (I), or by soil application, i.e.the compounds of the formula (I) according to the invention areintroduced in solid form (e.g. in the form of granules) into the locusof the plants. In the case of paddy rice crops, this can also be done bymetering the compound of the formula (I) in a solid application form(for example as granules) into a flooded paddy field.

Treatment of Seed

The control of animal pests by treating the seed of plants has beenknown for a long time and is the subject of continuous improvements.However, the treatment of seed entails a series of problems which cannotalways be solved in a satisfactory manner. Thus, it is desirable todevelop methods for protecting the seed and the germinating plant whichdispense with, or at least reduce considerably, the additionalapplication of pesticides during storage, after sowing or afteremergence of the plants. It is furthermore desirable to optimize theamount of active compound employed in such a way as to provide optimumprotection for the seed and the germinating plant from attack by animalpests, but without damaging the plant itself by the active compoundemployed. In particular, methods for the treatment of seed should alsotake into consideration the intrinsic insecticidal or nematicidalproperties of pest-resistant or -tolerant transgenic plants in order toachieve optimum protection of the seed and also the germinating plantwith a minimum of pesticides being employed.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants, from attack by pests,by treating the seed with one of the compounds of the formula (I). Themethod according to the invention for protecting seed and germinatingplants against attack by pests furthermore comprises a method where theseed is treated simultaneously in one operation or sequentially with acompound of the formula (I) and a mixing component. It also comprises amethod where the seed is treated at different times with a compound ofthe formula (I) and a mixing component.

The invention likewise relates to the use of the compounds of theformula (I) for the treatment of seed for protecting the seed and theresulting plant from animal pests.

Furthermore, the invention relates to seed which has been treated with acompound of the formula (I) according to the invention so as to affordprotection from animal pests. The invention also relates to seed whichhas been treated simultaneously with a compound of the formula (I) and amixing component. The invention furthermore relates to seed which hasbeen treated at different times with a compound of the formula (I) and amixing component. In the case of seed which has been treated atdifferent points in time with a compound of the formula (I) and a mixingcomponent, the individual substances may be present on the seed indifferent layers. Here, the layers comprising a compound of the formula(I) and mixing components may optionally be separated by an intermediatelayer. The invention also relates to seed where a compound of theformula (I) and a mixing component have been applied as component of acoating or as a further layer or further layers in addition to acoating.

Furthermore, the invention relates to seed which, after the treatmentwith a compound of the formula (I), is subjected to a film-coatingprocess to prevent dust abrasion on the seed.

One of the advantages encountered with a systemically acting compound ofthe formula (I) is the fact that, by treating the seed, not only theseed itself but also the plants resulting therefrom are, afteremergence, protected against animal pests. In this manner, the immediatetreatment of the crop at the time of sowing or shortly thereafter can bedispensed with.

It has to be considered a further advantage that by treatment of theseed with a compound of the formula (I), germination and emergence ofthe treated seed may be enhanced.

It is likewise to be considered advantageous that compounds of theformula (I) can be used in particular also for transgenic seed.

Furthermore, compounds of the formula (I) can be employed in combinationwith compositions or compounds of signalling technology, leading tobetter colonization by symbionts such as, for example, rhizobia,mycorrhizae and/or endophytic bacteria or fungi, and/or to optimizednitrogen fixation.

The compounds of the formula (I) are suitable for protection of seed ofany plant variety which is used in agriculture, in the greenhouse, inforests or in horticulture. In particular, this takes the form of seedof cereals (for example wheat, barley, rye, millet and oats), corn,cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola,oilseed rape, beets (for example sugarbeets and fodder beets), peanuts,vegetables (for example tomatoes, cucumbers, bean, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. The treatment of the seed of cereals (such as wheat, barley, ryeand oats), maize, soya beans, cotton, canola, oilseed rape and rice isof particular importance.

As already mentioned above, the treatment of transgenic seed with acompound of the formula (I) is also of particular importance. This takesthe form of seed of plants which, as a rule, comprise at least oneheterologous gene which governs the expression of a polypeptide with inparticular insecticidal and/or nematicidal properties. The heterologousgenes in transgenic seed can originate from microorganisms such asBacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter,Glomus or Gliocladium. The present invention is particularly suitablefor the treatment of transgenic seed which comprises at least oneheterologous gene originating from Bacillus sp. It is particularlypreferably a heterologous gene derived from Bacillus thuringiensis.

In the context of the present invention, the compound of the formula (I)is applied to the seed. Preferably, the seed is treated in a state inwhich it is stable enough to avoid damage during treatment. In general,the seed may be treated at any point in time between harvest and sowing.The seed usually used has been separated from the plant and freed fromcobs, shells, stalks, coats, hairs or the flesh of the fruits. Forexample, it is possible to use seed which has been harvested, cleanedand dried down to a moisture content which allows storage.Alternatively, it is also possible to use seed which, after drying, hasbeen treated with, for example, water and then dried again, for examplepriming. In the case of rice seed, it is also possible to use seed whichhas been soaked, for example in water to a certain stage of the riceembryo (‘pigeon breast stage’), stimulating the germination and a moreuniform emergence.

When treating the seed, care must generally be taken that the amount ofthe compound of the formula (I) applied to the seed and/or the amount offurther additives is chosen in such a way that the germination of theseed is not adversely affected, or that the resulting plant is notdamaged. This must be ensured particularly in the case of activecompounds which can exhibit phytotoxic effects at certain applicationrates.

In general, the compounds of the formula (I) are applied to the seed ina suitable formulation. Suitable formulations and processes for seedtreatment are known to the person skilled in the art.

The compounds of the formula (I) can be converted to the customary seeddressing formulations, such as solutions, emulsions, suspensions,powders, foams, slurries or other coating compositions for seed, andalso ULV formulations.

These formulations are prepared in a known manner, by mixing thecompounds of the formula (I) with customary additives such as, forexample, customary extenders and also solvents or diluents, colorants,wetting agents, dispersants, emulsifiers, antifoams, preservatives,secondary thickeners, adhesives, gibberellins and also water.

Colorants which may be present in the seed-dressing formulations whichcan be used in accordance with the invention are all colorants which arecustomary for such purposes. It is possible to use either pigments,which are sparingly soluble in water, or dyes, which are soluble inwater. Examples include the dyes known by the names Rhodamine B, C.I.Pigment Red 112 and C.I. Solvent Red 1.

Useful wetting agents which may be present in the seed dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are conventionally used for theformulation of agrochemically active compounds. Preference is given tousing alkylnaphthalenesulphonates, such as diisopropyl- ordiisobutylnaphthalenesulphonates.

Useful dispersants and/or emulsifiers which may be present in the seeddressing formulations usable in accordance with the invention are allnonionic, anionic and cationic dispersants conventionally used for theformulation of active agrochemical ingredients. Preference is given tousing nonionic or anionic dispersants or mixtures of nonionic or anionicdispersants. Suitable nonionic dispersants include in particularethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristryrylphenol polyglycol ethers, and the phosphated orsulphated derivatives thereof. Suitable anionic dispersants are inparticular lignosulphonates, polyacrylic acid salts andarylsulphonate/formaldehyde condensates.

Antifoams which may be present in the seed dressing formulations usablein accordance with the invention are all foam-inhibiting substancesconventionally used for the formulation of active agrochemicalingredients. Preference is given to using silicone antifoams andmagnesium stearate.

Preservatives which may be present in the seed dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.Cellulose derivatives, acrylic acid derivatives, xanthan, modified claysand finely divided silica are preferred.

Adhesives which may be present in the seed dressing formulations usablein accordance with the invention are all customary binders usable inseed dressing products. Polyvinylpyrrolidone, polyvinyl acetate,polyvinyl alcohol and tylose may be mentioned as being preferred.

Gibberellins which can be present in the seed-dressing formulationswhich can be used in accordance with the invention are preferably thegibberellins A1, A3 (=gibberellic acid), A4 and A7; gibberellic acid isespecially preferably used. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz- and Schiidlingsbekimpfungsmittel”, vol. 2,Springer Verlag, 1970, pp. 401-412).

The seed dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats, and triticale, and also the seed of maize, rice, oilseedrape, peas, beans, cotton, sunflowers, soya beans and beets, or else awide variety of different vegetable seed. The seed dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For treatment of seed with the seed dressing formulations usable inaccordance with the invention, or the use forms prepared therefrom byadding water, all mixing units usable customarily for the seed dressingare useful. Specifically, the procedure in the seed dressing is to placethe seed into a mixer, operated batch-wise or continously, to add theparticular desired amount of seed dressing formulations, either as suchor after prior dilution with water, and to mix everything until theformulation is distributed homogeneously on the seed. If appropriate,this is followed by a drying operation.

The application rate of the seed dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds of theformula (I) in the formulations and by the seed. The application ratesof the compound of the formula (I) are generally between 0.001 and 50 gper kilogram of seed, preferably between 0.01 and 15 g per kilogram ofseed.

Animal Health

In the animal health field, i.e. in the field of veterinary medicine,the compounds of the formula (I) are active against animal parasites, inparticular ectoparasites or endoparasites. The term endoparasitesincludes in particular helminths and protozoans, such as coccidia.Ectoparasites are typically and preferably arthropods, in particularinsects and acarids.

In the field of veterinary medicine the compounds of the formula (I) aresuitable, with favourable homeotherm toxicity, for controlling parasiteswhich occur in animal breeding and animal husbandry in livestock,breeding, zoo, laboratory, experimental and domestic animals. They areactive against all or specific stages of development of the parasites.

Agricultural livestock include, for example, mammals, such as sheep,goats, horses, donkeys, camels, buffaloes, rabbits, reindeers, fallowdeers, and in particular cattle and pigs; or poultry such as turkeys,ducks, geese, and in particular chickens; fish and crustaceans, forexample in aquaculture; and also insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets and in particular dogs, cats,cage birds, reptiles, amphibians and aquarium fish.

According to a preferred embodiment, the compounds of the formula (I)are administered to mammals.

According to another preferred embodiment, the compounds of the formula(I) are administered to birds, namely cage birds and in particularpoultry.

By using the compounds of the formula (I) to control animal parasites,it is intended to reduce or prevent illness, cases of deaths andperformance reductions (in the case of meat, milk, wool, hides, eggs,honey and the like), so that more economical and simpler animal keepingis made possible and better animal well-being is achievable.

The term “control” or “controlling” as used herein with regard to theanimal health field, means that the compounds of the formula (I) areeffective in reducing the incidence of the respective parasite in ananimal infected with such parasites to innocuous levels. Morespecifically, “controlling”, as used herein, means that the compound ofthe formula (I) is effective in killing the respective parasite,inhibiting its growth, or inhibiting its proliferation.

Arthropods include:

from the order of the Anoplurida, for example Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; fromthe order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.; from the order of the Diptera and thesuborders Nematocerina and Brachycerina, for example Aedes spp.,Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomusspp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp.,Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossinaspp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp.,Tipula spp.; from the order of the Siphonapterida, for example Pulexspp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllusspp.;

from the order of the Heteropterida, for example Cimex spp., Triatomaspp., Rhodnius spp., Panstrongylus spp.; as well as nuisance and hygienepests from the order of the Blattarida.

Arthropods furthermore include:

from the subclass of the Acari (Acarina) and the order of theMetastigmata, for example from the family of argasidae like Argas spp.,Ornithodorus spp., Otobius spp., from the family of Ixodidae like Ixodesspp., Amblyomma spp., Rhipicephalus (Boophilus) spp Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the originalgenus of multi-host ticks); from the order of mesostigmata likeDermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietiaspp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.;from the order of the Actinedida (Prostigmata), for example Acarapisspp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergatesspp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorusspp.; and from the order of the Acaridida (Astigmata), for exampleAcarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp.,Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp.,Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp.,Laminosioptes spp.

Parasitic Protozoa include:

Mastigophora (Flagellata) such as, for example, Trypanosomatidae, forexample, Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T.congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T.simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, suchas, for example, Trichomonadidae, for example, Giardia lamblia, G.canis.;Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example,Entamoeba histolytica, Hartmanellidae, for example, Acanthamoeba sp.,Harmanella sp.;

Apicomplexa (Sporozoa) such as Eimeridae, for example, Eimeriaacervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E.arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis, E.chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E.debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E.flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina,E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media,E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E.ninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans, E.phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec., E.stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii,Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis, I.rivolta, I. spec., I. suis, Cystisospora spec., Cryptosporidium spec.,in particular C. parvum; such as Toxoplasmadidae, for example,Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitiabesnoitii; such as Sarcocystidae, for example, Sarcocystis bovicanis, S.bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec., S.suihominis, such as Leucozoidae, for example, Leucozytozoon simondi,such as Plasmodiidae, for example, Plasmodium berghei, P. falciparum, P.malariae, P. ovale, P. vivax, P. spec., such as Piroplasmea, forexample, Babesia argentina, B. bovis, B. canis, B. spec., Theileriaparva, Theileria spec., such as Adeleina, for example, Hepatozoon canis,H. spec.

Pathogenic endoparasites, which are helminths, include Platyhelmintha(e.g. Monogenea, cestodes and trematodes), nematodes, Acanthocephala,and Pentastoma, including:

Monogenea: e.g.: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.;

Cestodes: from the order of the Pseudophyllidea for example:Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligulaspp., Bothridium spp., Diplogonoporus spp.;from the order of the Cyclophyllida for example: Mesocestoides spp.,Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomaspp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaeniaspp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp.,Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp.,Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp.,Joyeuxiella spp., Diplopylidium spp.;Trematodes: from the class of the Digenea for example: Diplostomum spp.,Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp.,Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp.,Leucochloridium spp., Brachylaima spp., Echinostoma spp.,Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciolaspp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp.,Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoronspp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp.,Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimusspp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimusspp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchisspp. Metorchis spp., Heterophyes spp., Metagonimus spp.;

Nematodes: Trichinellida zum Beispiel: Trichuris spp., Capillaria spp.,Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinellaspp.;

from the order of the Tylenchida for example: Micronema spp.,Strongyloides spp.;from the order of the Rhabditida for example: Strongylus spp.,Triodontophorus spp., Oesophagodontus spp., Trichonema spp.,Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp.,Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp.,Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp.,Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp.,Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muelleriusspp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp.,Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerusspp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp.,Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagiaspp., Teladorsagia spp., Marshallagia spp., Cooperia spp.,Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp.,Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.;from the order of the Spirurida, for example: Oxyuris spp., Enterobiusspp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.;Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp.,Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp.,Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp.,Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp.,Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoidesspp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.;Acanthocephala: from the order of the Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order of thePolymorphida, for example: Filicollis spp.; from the order of theMoniliformida, for example: Moniliformis spp.;from the order of the Echinorhynchida, for example, Acanthocephalusspp., Echinorhynchus spp., Leptorhynchoides spp.;Pentastoma: from the order of the Porocephalida, for example, Linguatulaspp.

In the veterinary field and in animal keeping, administration of thecompounds of the formula (I) is carried out by methods generally knownin the art, such as enterally, parenterally, dermally or nasally in theform of suitable preparations. Administration can be carried outprophylactically or therapeutically.

Thus, one embodiment of the present invention refers to the use of acompound of the formula (I) as medicament.

A further aspect refers to the use of a compound of the formula (I) asan antiendoparasitic agent, in particular a helminthicidal agent orantiprotozoic agent. Compounds of the formula (I) are suitable for useas an antiendoparasitic agent, in particular a helminthicidal agent orantiprotozoic agent, for example in animal husbandry, in animalbreeding, in animal housing and in the hygiene sector.

A further aspect in turn relates to the use of a compound of the formula(I) as an antiectoparasitic, in particular an arthropodicide such as aninsecticide or an acaricide. A further aspect relates to the use of acompound of the formula (I) as an antiectoparasitic, in particular anarthropodicide such as an insecticide or an acaricide, for example inanimal husbandry, in animal breeding, in stables or in the hygienesector.

Anthelmintic Mixing Components

The following anthelmintic mixing components may be mentioned by way ofexample:

Anthelmintically active compounds including trematicidally andcestocidally active compounds:from the class of the macrocyclic lactones, for example: abamectin,doramectin, emamectin, eprinomectin, ivermectin, milbemycin, moxidectin,nemadectin, selamectin;from the class of the benzimidazoles and probenzimidazoles, for example:albendazole, albendazole-sulphoxide, cambendazole, cyclobendazole,febantel, fenbendazole, flubendazole, mebendazole, netobimin,oxfendazole, oxibendazole, parbendazole, thiabendazole, thiophanate,triclabendazole;from the class of the cyclooctadepsipeptides, for example: emodepside,PF1022;from the class of the aminoacetonitrile derivatives, for example:monepantel;from the class of the tetrahydropyrimidines, for example: morantel,pyrantel, oxantel;from the class of the imidazothiazoles, for example: butamisole,levamisole, tetramisole;from the class of the salicylanilides, for example: bromoxanide,brotianide, clioxanide, closantel, niclosamide, oxyclozanide,rafoxanide, tribromsalan;from the class of the paraherquamides, for example: derquantel,paraherquamide;from the class of the aminophenylamidines, for example: amidantel,deacylated amidantel (dAMD), tribendimidine;from the class of the organophosphates, for example: coumaphos,crufomate, dichlorvos, haloxone, naphthalofos, trichlorfon;from the class of the substituted phenols, for example: bithionol,disophenol, hexachlorophene, niclofolan, meniclopholan, nitroxynil;from the class of the piperazinones, for example: praziquantel,epsiprantel;from various other classes, for example: amoscanate, bephenium,bunamidine, clonazepam, clorsulon, diamfenetid, dichlorophen,diethylcarbamazine, emetine, hetolin, hycanthone, lucanthone, Miracil,mirasan, niclosamide, niridazole, nitroxynil, nitroscanate, oltipraz,omphalotin, oxamniquin, paromomycin, piperazine, resorantel.

Vector Control

The compounds of the formula (I) can also be used in vector control. Forthe purpose of the present invention, a vector is an arthropod, inparticular an insect or arachnid, capable of transmitting pathogens suchas, for example, viruses, worms, single-cell organisms and bacteria froma reservoir (plant, animal, human, etc.) to a host. The pathogens can betransmitted either mechanically (for example trachoma by non-stingingflies) to a host, or by injection (for example malaria parasites bymosquitoes) into a host.

Examples of vectors and the diseases or pathogens they transmit are:

1) Mosquitoes

-   -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, filariasis, other viral diseases,        transmission of worms;    -   Aedes: yellow fever, dengue fever, filariasis, other viral        diseases;    -   Simuliidae: transmission of worms, in particular Onchocerca        volvulus;        2) Lice: skin infections, epidemic typhus;        3) Fleas: plague, endemic typhus;        4) Flies: sleeping sickness (trypanosomiasis); cholera, other        bacterial diseases;        5) Mites: acariosis, epidemic typhus, rickettsialpox,        tularaemia, Saint Louis encephalitis, tick-borne encephalitis        (TBE), Crimean-Congo haemorrhagic fever, borreliosis;        6) Ticks: borellioses such as Borrelia duttoni, tick-borne        encephalitis, Q fever (Coxiella burnetii), babesioses (Babesia        canis canis).

Examples of vectors in the sense of the present invention are insects,for example aphids, flies, leafhoppers or thrips, which are capable oftransmitting plant viruses to plants. Other vectors capable oftransmitting plant viruses are spider mites, lice, beetles andnematodes.

Further examples of vectors in the sence of the present invention areinsects and arachnids such as mosquitoes, in particular of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dirus (malaria) and Culex, lice, fleas, flies, mites and ticks capableof transmitting pathogens to animals and/or humans.

Vector control is also possible if the compounds of the formula (I) areresistance-breaking.

Compounds of the formula (I) are suitable for use in the prevention ofdiseases and/or pathogens transmitted by vectors. Thus, a further aspectof the present invention is the use of compounds of the formula (I) forvector control, for example in agriculture, in horticulture, in gardensand in leisure facilities, and also in the protection of materials andstored products.

Protection of Industrial Materials

The compounds of the formula (I) are suitable for protecting industrialmaterials against attack or destruction by insects, for example from theorders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera andZygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protecting wood isparticularly preferred.

In a further embodiment, the compounds of the formula (I) are usedtogether with at least one further insecticide and/or at least onefungicide.

In a further embodiment, the compounds of the formula (I) are present asa ready-to-use pesticide, i.e. they can be applied to the material inquestion without further modifications. Suitable further insecticides orfungicides are in particular those mentioned above.

Surprisingly, it has also been found that the compounds of the formula(I) can be employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signalling systems, against fouling. Likewise,the compounds of the formula (I), alone or in combinations with otheractive compounds, can be used as antifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of the formula (I) are suitable for controlling animalpests in the hygiene sector. In particular, the invention can be appliedin the domestic sector, in the hygiene sector and in the protection ofstored products, especially for controlling insects, arachnids and mitesencountered in enclosed spaces such as dwellings, factory halls,offices, vehicle cabins. For controlling animal pests, the compounds ofthe formula (I) are used alone or in combination with other activecompounds and/or auxiliaries. They are preferably used in domesticinsecticide products. The compounds of the formula (I) are effectiveagainst sensitive and resistant species, and against all developmentalstages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand Diplopoda, from the class Insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

They are used, for example, in aerosols, pressure-free spray products,for example pump and atomizer sprays, automatic fogging systems,foggers, foams, gels, evaporator products with evaporator tablets madeof cellulose or plastic, liquid evaporators, gel and membraneevaporators, propeller-driven evaporators, energy-free, or passive,evaporation systems, moth papers, moth bags and moth gels, as granulesor dusts, in baits for spreading or in bait stations.

The various aspects of the invention will now be illustrated withreference to the following production and use examples in a non limitingmanner.

PREPARATION EXAMPLES

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of formula (I) may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of formula (I). One skilled in theart will also recognize that it may be necessary to perform acombination of the steps illustrated in the above schemes in an orderother than that implied by the particular sequence presented to preparethe compounds of formula (I).

One skilled in the art will also recognize that compounds of formula (I)and the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following Synthesis Examples are, therefore, to beconstrued as merely illustrative, and not limiting of the disclosure inany way whatsoever. Steps in the following Synthesis Examples illustratea procedure for each step in an overall synthetic transformation, andthe starting material for each step may not have necessarily beenprepared by a particular preparative run whose procedure is described inother Examples or Steps.

¹H-NMR data

¹H-NMR-data were determined with a Bruker Avance 400 equipped with aflow cell (60 μl volume) or with a Bruker AVIII 400 equipped with 1.7 mmcryo-CPTCI probe head or with a Bruker AVII 600 (600.13 MHz) equippedwith a cyroTCI probe head or with a Bruker AVIII 600 (601.6 MHz)equipped with a cryo CPMNP probe head with tetramethylsilane asreference (0.0) and the solvents CD₃CN, CDCl₃, [D₆]-DMSO.

¹H-NMR-data of selected examples are listed in classic format (chemicalshift δ, multiplicity, number of hydrogen atoms) or as NMR-peak-lists.

¹H NMR spectra are reported in ppm downfield from tetramethylsilane.

“s” means singlet, “d” means doublet, “dd” means doublet of doublets,“t” means triplet, “q” means quartet, “br s” means broad singlet, “m”means multiplet.

NMR-peak-lists:

If NMR-data of selected examples are provided in form of ¹H-NMR-peaklists, then for every peak first the chemical shift δ in ppm and then,separated by a blank, the intensity of the signal in round brackets islisted. Between the δ-value-signal intensity pairs are semicolons asdelimiters.

The peak list of an example is therefore listed as: δ₁ (intensity₁); δ₂(intensity₂); . . . ; δ_(i) (intensity_(i)); . . . ;δ_(n)(intensity_(n)).

Intensity of sharp signals correlates with the height of the signals ina printed example of a NMR spectrum in cm and shows the real relationsof signal intensities. From broad signals several peaks or the middle ofthe signal and their relative intensity in comparison to the mostintensive signal in the spectrum can be shown.

For calibrating chemical shift for 1H spectra, we use tetramethylsilaneand/or the chemical shift of the solvent used, especially in the case ofspectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilanepeak can occur but not necessarily.

The 1H-NMR peak lists are similar to classical 1H-NMR prints and containtherefore usually all peaks, which are listed at classicalNMR-interpretation.

Additionally they can show like classical 1H-NMR prints signals ofsolvents, stereoisomers of the target compounds, which are also objectof the invention, and/or peaks of impurities.

To show compound signals in the delta-range of solvents and/or water theusual peaks of solvents, for example peaks of DMSO in DMSO-D₆ and thepeak of water are shown in our 1H-NMR peak lists and have usually onaverage a high intensity.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities have usually on average a lower intensity than the peaks oftarget compounds (for example with a purity >90%).

Such stereoisomers and/or impurities can be typical for the specificpreparation process. Therefore their peaks can help to recognize thereproduction of our preparation process via“side-products-fingerprints”.

An expert, who calculates the peaks of the target compounds with knownmethods (MestreC, ACD-simulation, but also with empirically evaluatedexpectation values) can isolate the peaks of the target compounds asneeded optionally using additional intensity filters. This isolationwould be similar to relevant peak picking at classical ¹H-NMRinterpretation.

Further details of NMR-data description with peak lists you find in thepublication “Citation of NMR Peaklist Data within patent applications”of the Research Disclosure Database Number 564025.

The solvent, in which the NMR-spectrum was measured, is specified insquared brackets.

Synthesis Example 1 Preparation ofN-[(2-chlorophenyl)sulfonyl]-5-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxamide(table 2, example (I-1))

To 69 mg 5-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid(0.30 mmol) was added a solution of 4-(dimethylamino)pyridine (110 mg,0.90 mmol) and 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimidehydrochloride (205 mg, 0.90 mmol) in dichloromethane (9 mL). Thereaction mixture was stirred for 15 min, 2-chloro-benzenesulfonamide(57.5 mg, 0.30 mmol) was added, and the reaction mixture was stirred atroom temperature overnight. Dichloromethane (50 mL) was then added, themixture was washed with 1 N hydrochloric acid (50 mL). The aqueous phasewas reextracted two times with dichloromethane, all organic phases werecombined and dried over magnesium sulfate. The solvent was evaporatedand the remaining solid was rinsed with diethyl ether to afford 121 mg(purity 90%, 89.7%) of the title compound, a compound of the presentinvention, as a colorless solid, ¹H-NMR, Table 3.

Preparation of Intermediates of General Formula (II) Preparation of4-chloro-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid(II-1) Step 1: Preparation ofN-amino-3-chloro-5-trifluoromethyl-pyridinium p-tosylate

To a solution of 1-[(aminooxy)sulfonyl]-4-methylbenzene (15 g, 80 mmol)in dichloromethane was added 3-chloro-5-(trifluoromethyl)pyridine (9.9g, 68 mmol), and the mixture stirred at 20° C. for 2 h. Then the solventwas removed under reduced pressure to give 7.4 g of the desired productas a white solid, which was used directly in the next step withoutfurther purification.

See FIG. 1, which depicts the ¹H-NMR spectrum ofN-amino-3-chloro-5-trifluoromethyl-pyridinium p-tosylate ([D₆]-DMSO, 400MHz)

Step 2: Preparation of dimethyl4-chloro-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2,3-dicarboxylate(isomer A)

To a solution of N-amino-3-chloro-5-trifluoromethyl-pyridiniump-tosylate (28.5 g, 77 mmol) in dimethylformamide (300 mL) was addeddimethyl acetylenedicarboxylate (16 g, 116 mmol) and potassium carbonate(21 g, 155 mmol) at 0° C. The resulting mixture was stirred at roomtemperature overnight with the existence of oxygene via introducing asteam of dry air to the reaction with a pressure pump. Thin layerchromatography check showed complete consumption of the startingmaterial, water and ethyl acetate was added to the mixture and theorganic phase was separated and combined, dried over sodium sulfate,filtered, concentrated, and purified by silica gel column chromatography(n-hexane:EtOAc=6:1) to isolate the two isomers separately. Desireddimethyl4-chloro-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2,3-dicarboxylate(isomer A, 7.1 g) was obtained as an red solid. The structure of isomerswas elucidated and characterized by ¹H-NMR, ¹³C-NMR, HMBC((Heteronuclear Multiple Bond Correlation) and HSQC (HeteronuclearSingle Quantum Correlation) based on the J(C,F) coupling patterns inboth isomers.

See FIG. 2, which depicts the ¹H-NMR spectrum of dimethyl4-chloro-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2,3-dicarboxylate(CDCl₃, 400 MHz)

Step 3: Preparation of4-chloro-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid(II-1)

A solution of dimethyl4-chloro-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2,3-dicarboxylate(7.1 g, 21 mmol) in aq. sulfuric acid (150 mL, v/v 50%) was heated to90° C. for 24 h. Then the mixture was cooled to room temperature,neutralized with 5 N NaOH followed by treatment with 2 N aq. HCl untilpH=2-3 was reached. The mixture was extracted with ethyl acetate (3×80mL) and the combined organic phases were washed with brine, dried oversodium sulfate, filtered, and evaporated, followed by re-crystallizationfrom dichloromethane/n-hexane (2/1, v/v) to give 3.7 g pure targetcompound4-chloro-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid(II-1) as a white solid.

See FIG. 3, which depicts the ¹H-NMR spectrum of4-chloro-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid(II-1) ([D₆]-DMSO, 400 MHz)

According to the method described above, the following compounds ofgeneral formula (I) have been prepared.

Compounds of General Formula (I):

TABLE 2 (I)

Example R¹ n Q Remarks I-1 5-CF₃ 1

NMR I-2 4-Cl, 6-CF₃ 2

NMR I-3 4-Cl, 6-CF₃ 2

NMR I-4 4-Cl, 6-CF₃ 2

NMR I-5 4-Cl, 6-CF₃ 2

NMR I-6 4-Cl, 6-CF₃ 2

NMR I-7 4-Cl, 6-CF₃ 2

NMR I-8 4-Cl, 6-CF₃ 2

NMR I-9 4-Cl, 6-CF₃ 2

NMR I-10 4-Cl, 6-CF₃ 2

NMR I-11 4-Cl, 6-CF₃ 2

NMR I-12 4-Cl, 6-CF₃ 2

NMR I-13 4-Cl, 6-CF₃ 2

NMR I-14 4-Cl, 6-CF₃ 2

NMR I-15 4-Cl, 6-CF₃ 2 - - -CH₃ NMR I-16 4-Cl, 6-CF₃ 2 - - -Et NMR I-174-Cl, 6-CF₃ 2

NMR I-18 4-Cl, 6-CF₃ 2

NMR I-19 5-CF₃, 7-Cl 2

NMR I-20 5-CF₃, 7-Cl 2

NMR I-21 5-CF₃, 7-Cl 2

NMR I-22 5-CF₃, 7-Cl 2

NMR I-23 5-CF₃, 7-Cl 2

NMR I-24 5-CF₃, 7-Cl 2

NMR I-25 5-CF₃ 1

NMR I-26 5-CF₃ 1

NMR I-27 5-CF₃ 1

NMR I-28 5-CF₃, 7-Cl 2 - - -CH₃ NMR I-29 5-CF₃ 1

NMR I-30 5-CF₃, 7-Cl 2

NMR I-31 5-CF₃, 7-Cl 2

NMR I-32 5-CF₃, 7-Cl 2 - - -Et NMR I-33 5-CF₃ 1

NMR I-34 5-CF₃ 1

NMR I-35 5-CF₃ 1

NMR I-36 5-CF₃ 1

NMR I-37 5-CF₃ 1

NMR I-38 5-CF₃ 1

NMR I-39 5-CF₃ 1

NMR I-40 5-CF₃ 1

NMR I-41 5-CF₃ 1

NMR I-42 5-CF₃ 1

NMR I-43 5-CF₃ 1

NMR I-44 5-CF₃, 7-Cl 2

NMR I-45 5-CF₃, 7-Cl 2

NMR I-46 5-Cl, 7-Cl 2

NMR I-47 5-Cl, 7-Cl 2

NMR I-48 5-Cl, 7-Cl 2

NMR I-49 5-Cl, 7-Cl 2

NMR I-50 6-CF₃ 2

NMR I-51 6-CF₃ 2

NMR I-52 6-CF₃ 2

NMR I-53 7-CF₃ 2

NMR I-54 5-CF₃, 7-Cl 2 - - -CF₂—CH₃ NMR I-55 5-CF₃, 7-Cl 2 - - -CF₃ NMRI-56 5-Cl, 7-Cl 2

NMR I-57 5-Cl, 7-Cl 2

NMR I-58 5-Cl, 7-Cl 2

NMR I-59 5-Cl, 7-Cl 2

NMR I-60 5-Cl, 7-Cl 2

NMR I-61 5-Cl, 7-Cl 2

NMR I-62 5-CF₃, 7-Cl 2

NMR I-63 5-CF₃, 7-Cl 2

NMR I-64 5-CF₃, 7-Cl 2

NMR I-65 5-CF₃, 7-Cl 2

NMR I-66 5-Cl, 7-Cl 2

NMR I-67 5-Cl, 7-Cl 2

NMR I-68 5-Cl, 7-Cl 2

NMR I-69 5-Cl, 7-Cl 2

NMR I-70 5-CF₃, 7-Cl 2

NMR I-71 5-CF₃, 7-Cl 2

NMR I-72 5-CF₃, 7-Cl 2

NMR I-73 5-CF₃ 1

NMR I-74 5-CF₃, 7-Cl 2

NMR I-75 5-Cl, 7-Cl 2

NMR I-76 5-Cl, 7-Cl 2

NMR I-77 5-CF₃, 7-Cl 2

NMR I-78 5-CF₃ 1

NMR Z = O, R² and R³ are H and Q = substituted aryl, alkyl or cycloalkylas indicated

¹H-NMR Data of Compounds of General Formula (I):

TABLE 3 Example NMR data I-1 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 7.681 (0.3); 7.508 (0.4); 3.187 (0.4); 3.170 (16.0);2.512 (2.8); 2.508 (5.6); 2.503 (7.5); 2.499 (5.6); 2.494 (2.8); 0.008(0.4); 0.000 (9.6); −0.009 (0.4). I-2 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 9.449 (10.2); 9.086 (9.9); 9.085 (9.9);8.798 (9.0); 7.924 (12.6); 7.475 (11.3); 5.758 (16.0); 4.540 (0.4);4.525 (0.4); 4.172 (0.6); 4.045 (0.6); 3.975 (0.6); 3.817 (0.5); 3.801(0.4); 3.787 (0.4); 2.676 (0.6); 2.672 (1.0); 2.667 (0.6); 2.507(178.2); 2.502 (241.8); 2.498 (190.2); 2.334 (1.9); 2.329 (2.3); 2.325(2.0); 2.110 (0.4); 2.076 (0.4); 1.575 (0.7); 1.570 (0.4); 1.352 (0.4);1.259 (0.4); 1.233 (0.8); 1.188 (1.7); 0.008 (0.4); 0.000 (14.1); −0.008(1.1). I-3 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ =9.436 (2.2); 7.928 (2.8); 7.652 (2.8); 7.644 (2.8); 7.593 (2.4); 7.581(2.5); 7.571 (2.8); 7.316 (1.3); 7.308 (1.3); 7.294 (1.2); 7.286 (1.1);5.759 (0.8); 3.870 (16.0); 2.671 (0.4); 2.511 (22.7); 2.507 (44.0);2.502 (57.7); 2.498 (42.9); 2.494 (21.9); 2.329 (0.4); 0.000 (2.8). I-4¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 9.437 (9.6);8.415 (5.6); 8.396 (6.2); 8.024 (4.1); 8.005 (6.5); 7.991 (2.3); 7.975(5.3); 7.956 (4.4); 7.941 (4.6); 7.922 (16.0); 7.905 (2.1); 7.529 (9.4);7.388 (0.5); 5.759 (4.0); 3.891 (0.4); 3.687 (0.7); 2.676 (1.4); 2.672(1.9); 2.667 (1.4); 2.525 (5.9); 2.512 (102.7); 2.507 (200.2); 2.503(260.4); 2.498 (190.6); 2.494 (93.7); 2.334 (1.3); 2.330 (1.7); 2.325(1.2); 1.584 (0.4); 1.576 (0.4); 1.546 (0.4); 0.000 (3.2). I-5 ¹H-NMR,Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 9.429 (13.3); 8.185(7.8); 8.166 (8.3); 7.922 (16.0); 7.872 (3.4); 7.853 (7.2); 7.836 (4.5);7.833 (4.5); 7.670 (5.7); 7.651 (9.7); 7.632 (4.9); 7.611 (6.6); 7.591(5.7); 7.548 (13.2); 3.892 (0.5); 3.868 (0.5); 3.843 (0.5); 3.841 (0.5);3.823 (0.5); 3.750 (0.7); 3.744 (0.7); 3.718 (0.8); 3.693 (0.8); 3.661(0.9); 3.639 (0.9); 3.629 (0.9); 3.604 (0.9); 3.579 (1.0); 3.560 (0.9);3.543 (0.9); 3.507 (1.0); 3.448 (0.9); 3.391 (0.7); 3.382 (0.7); 3.362(0.7); 3.314 (0.6); 3.245 (0.5); 3.161 (0.4); 2.672 (2.1); 2.503(286.4); 2.330 (2.0); 2.076 (1.0); 1.576 (3.0); 0.000 (3.1). I-6 ¹H-NMR,Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 9.439 (12.7); 9.437(12.7); 8.219 (7.9); 8.216 (8.3); 8.200 (8.7); 8.196 (8.6); 7.928(16.0); 7.747 (2.1); 7.743 (2.3); 7.727 (6.3); 7.709 (7.3); 7.706 (7.0);7.686 (12.8); 7.670 (5.6); 7.666 (4.6); 7.659 (6.3); 7.655 (5.0); 7.639(7.9); 7.622 (3.8); 7.618 (3.3); 7.588 (13.0); 7.422 (0.4); 5.759(10.2); 3.691 (0.8); 3.428 (2.8); 3.128 (0.5); 3.053 (0.3); 2.676 (1.9);2.672 (2.5); 2.667 (1.8); 2.524 (8.2); 2.511 (136.7); 2.507 (258.7);2.502 (331.6); 2.498 (240.2); 2.334 (1.6); 2.329 (2.1); 2.325 (1.5);0.000 (3.7). I-7 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ= 9.564 (0.9); 9.433 (7.5); 9.431 (7.5); 7.918 (9.1); 7.802 (0.8); 7.787(1.7); 7.781 (1.7); 7.766 (2.9); 7.750 (1.7); 7.745 (1.7); 7.730 (0.8);7.496 (7.9); 7.384 (0.5); 7.363 (0.4); 7.339 (5.2); 7.316 (8.0); 7.293(4.5); 7.221 (1.3); 7.219 (1.3); 4.064 (0.3); 4.046 (0.3); 4.021 (0.3);3.988 (0.4); 3.960 (0.4); 3.939 (0.4); 3.918 (0.4); 3.891 (0.5); 3.862(0.4); 3.852 (0.4); 3.844 (0.4); 3.827 (0.4); 3.818 (0.4); 3.798 (0.4);3.779 (0.4); 3.772 (0.4); 3.767 (0.4); 3.759 (0.4); 3.752 (0.4); 3.744(0.4); 3.713 (0.5); 3.689 (0.4); 3.677 (0.4); 3.644 (0.4); 3.621 (0.4);3.589 (0.4); 3.568 (0.3); 2.676 (1.1); 2.672 (1.5); 2.667 (1.2); 2.507(153.3); 2.503 (196.7); 2.498 (149.6); 2.334 (1.0); 2.329 (1.3); 2.325(1.0); 2.076 (0.9); 1.583 (16.0); 1.333 (0.4); 1.317 (0.4); 0.930 (0.5);0.000 (1.9). I-8 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ= 9.457 (2.4); 7.956 (1.6); 7.952 (1.7); 7.936 (1.9); 7.931 (2.3); 7.928(3.2); 7.713 (0.7); 7.709 (0.8); 7.691 (1.4); 7.674 (0.9); 7.670 (0.9);7.632 (3.2); 7.255 (2.1); 7.234 (1.9); 7.191 (1.1); 7.173 (2.0); 7.153(1.0); 3.860 (16.0); 3.339 (3.9); 2.676 (0.3); 2.671 (0.4); 2.524 (1.4);2.511 (25.9); 2.507 (49.8); 2.502 (64.4); 2.498 (47.0); 2.493 (23.0);2.329 (0.4); 0.000 (0.4). I-9 ¹H-NMR, Solvent CD₃CN, spectrometer: 600MHz: δ = 8.926 (8.4); 8.924 (8.6); 8.090 (2.1); 8.086 (15.0); 8.083(6.2); 8.075 (5.7); 8.071 (16.0); 7.638 (2.3); 7.634 (16.0); 7.630(6.4); 7.622 (5.5); 7.619 (14.9); 7.595 (0.4); 7.584 (10.4); 7.582(10.8); 7.257 (13.2); 7.256 (13.6); 7.107 (0.3); 5.447 (1.1); 2.052(0.3); 1.966 (1.8); 1.958 (3.1); 1.953 (4.2); 1.950 (18.9); 1.946(32.5); 1.941 (46.9); 1.937 (32.8); 1.933 (17.0); 1.601 (4.9); 1.576(0.9); 1.266 (0.4); 0.005 (1.3); 0.000 (29.0); −0.006 (1.4). I-10¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 9.433 (3.1);8.088 (2.0); 8.085 (2.1); 8.068 (2.2); 8.065 (2.2); 7.930 (4.0); 7.627(0.8); 7.624 (0.9); 7.608 (2.0); 7.605 (2.1); 7.590 (1.4); 7.587 (1.3);7.532 (5.0); 7.494 (1.3); 7.475 (2.1); 7.457 (0.9); 7.431 (2.2); 7.412(1.9); 5.757 (0.6); 3.411 (0.4); 3.394 (0.4); 2.673 (0.4); 2.636 (16.0);2.526 (0.9); 2.512 (18.6); 2.508 (37.0); 2.504 (48.3); 2.499 (35.0);2.495 (17.0); 1.756 (0.4); 0.000 (0.7). I-11 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 9.428 (11.7); 9.426 (11.2); 8.135 (13.6);8.129 (13.8); 7.916 (14.9); 7.914 (14.2); 7.821 (5.7); 7.815 (5.4);7.800 (8.6); 7.793 (8.3); 7.721 (16.0); 7.700 (10.5); 7.522 (13.8);3.187 (0.6); 2.512 (55.8); 2.508 (120.5); 2.504 (164.9); 2.499 (128.9);2.495 (72.6); 2.335 (1.6); 2.330 (1.9); 2.326 (1.6); 1.757 (0.6); 1.546(0.5); 0.000 (3.6). I-12 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95MHz: δ = 9.444 (11.1); 9.442 (11.1); 8.317 (0.3); 8.013 (6.8); 8.008(13.0); 8.003 (8.8); 7.985 (6.6); 7.965 (7.2); 7.924 (14.2); 7.922(14.2); 7.830 (4.6); 7.827 (4.4); 7.825 (4.1); 7.812 (5.7); 7.810 (6.1);7.807 (6.1); 7.711 (8.4); 7.691 (12.9); 7.671 (5.5); 7.447 (16.0); 5.758(10.7); 3.187 (1.9); 2.772 (1.1); 2.760 (1.2); 2.676 (1.2); 2.672 (1.7);2.667 (1.2); 2.663 (0.5); 2.525 (5.3); 2.512 (100.2); 2.507 (200.5);2.503 (264.5); 2.498 (194.2); 2.494 (96.4); 2.339 (0.8); 2.334 (1.4);2.330 (1.9); 2.325 (1.4); 2.321 (0.8); 2.076 (0.6); 1.755 (1.3); 1.546(0.4); 1.006 (0.4); 0.988 (0.9); 0.970 (0.4); 0.000 (6.4). I-13 ¹H-NMR,Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 9.443 (10.8); 9.441(10.9); 8.041 (14.0); 8.023 (16.0); 8.019 (11.6); 7.927 (13.9); 7.926(13.9); 7.758 (2.5); 7.739 (7.8); 7.721 (5.9); 7.677 (11.4); 7.657(15.7); 7.639 (6.0); 7.474 (16.0); 7.319 (0.4); 7.202 (0.4); 5.758(11.5); 3.892 (0.4); 3.637 (0.4); 3.402 (1.3); 2.676 (1.5); 2.672 (2.0);2.667 (1.5); 2.511 (117.5); 2.507 (218.7); 2.502 (278.4); 2.498 (202.5);2.494 (100.2); 2.334 (1.3); 2.329 (1.8); 2.325 (1.3); 2.076 (0.5); 1.755(0.9); 1.576 (4.9); 1.545 (0.8); 1.309 (0.3); 0.008 (1.4); 0.000 (29.6);−0.008 (1.2). I-14 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz:δ = 9.427 (8.6); 9.425 (8.5); 8.316 (0.5); 8.201 (16.0); 7.920 (16.0);7.912 (11.4); 7.514 (8.3); 7.219 (0.4); 7.217 (0.4); 5.757 (10.0); 2.677(0.8); 2.672 (1.2); 2.668 (0.8); 2.525 (2.3); 2.512 (76.8); 2.507(158.4); 2.503 (212.1); 2.498 (157.9); 2.494 (80.1); 2.334 (1.2); 2.330(1.6); 2.325 (1.3); 1.755 (0.6); 1.584 (4.8); 0.146 (0.5); 0.008 (3.8);0.000 (132.9); −0.008 (6.0); −0.150 (0.7). I-15 ¹H-NMR, Solvent[D₆]-DMSO, spectrometer: 399.95 MHz: δ = 12.425 (0.4); 9.491 (9.5);7.947 (12.2); 7.578 (16.0); 3.580 (0.3); 3.407 (58.8); 3.352 (3.0);3.231 (0.5); 2.676 (0.6); 2.672 (0.8); 2.507 (98.4); 2.503 (124.9);2.499 (93.8); 2.334 (0.6); 2.330 (0.8); 2.326 (0.6); 1.755 (0.3); 0.000(17.3) I-16 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ =9.493 (4.0); 9.490 (3.9); 7.949 (5.2); 7.946 (5.1); 7.581 (7.0); 7.579(6.9); 3.565 (1.8); 3.547 (6.1); 3.528 (6.2); 3.510 (1.9); 3.338 (4.6);2.676 (0.4); 2.672 (0.6); 2.667 (0.4); 2.525 (1.8); 2.512 (33.4); 2.507(65.9); 2.503 (85.4); 2.498 (60.7); 2.494 (28.6); 2.334 (0.4); 2.329(0.6); 2.325 (0.4); 1.297 (7.0); 1.279 (16.0); 1.261 (6.8); 0.008 (0.6);0.000 (15.5); −0.009 (0.5). I-17 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 12.379 (0.9); 9.483 (10.3); 8.316 (0.4);7.948 (13.2); 7.553 (16.0); 5.757 (5.2); 3.337 (14.4); 3.168 (1.4);3.164 (1.3); 3.152 (2.5); 3.144 (2.8); 3.132 (4.7); 3.120 (2.9); 3.113(2.7); 3.100 (1.3); 2.676 (1.1); 2.671 (1.4); 2.667 (1.1); 2.507(173.3); 2.502 (220.2); 2.498 (161.3); 2.329 (1.4); 2.325 (1.0); 1.214(1.8); 1.199 (6.1); 1.193 (8.1); 1.184 (10.2); 1.174 (3.9); 1.157 (5.4);1.148 (7.1); 1.142 (7.1); 1.128 (7.7); 1.108 (1.7); 0.000 (31.4); −0.008(1.3). I-18 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ =9.413 (7.2); 9.410 (7.3); 8.316 (0.6); 7.911 (8.7); 7.909 (8.7); 7.672(5.8); 7.668 (7.0); 7.650 (16.0); 7.608 (5.9); 7.591 (4.0); 7.586 (3.1);7.569 (2.1); 7.519 (5.8); 3.929 (0.5); 3.892 (0.4); 3.802 (0.4); 3.785(0.4); 3.768 (0.4); 3.729 (0.5); 3.712 (0.6); 3.675 (0.5); 3.668 (0.5);3.639 (0.5); 3.609 (0.5); 3.594 (0.5); 3.579 (0.5); 3.506 (0.6); 3.499(0.5); 3.393 (0.5); 3.355 (0.4); 3.303 (0.3); 3.187 (1.6); 3.010 (0.4);2.770 (1.3); 2.757 (1.4); 2.676 (1.2); 2.671 (1.7); 2.667 (1.1); 2.545(0.4); 2.542 (0.7); 2.525 (3.3); 2.511 (83.5); 2.507 (170.6); 2.502(224.9); 2.498 (161.6); 2.493 (77.2); 2.334 (1.1); 2.329 (1.5); 2.325(1.1); 2.075 (2.5); 1.235 (0.6); 1.006 (0.5); 0.988 (1.0); 0.970 (0.5);0.146 (1.0); 0.008 (9.0); 0.000 (254.3); −0.009 (8.7); −0.025 (0.4);−0.032 (0.3); −0.150 (1.1). I-19 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 8.496 (7.2); 8.228 (4.4); 8.224 (4.8);8.208 (4.8); 8.204 (5.1); 7.813 (8.1); 7.809 (8.3); 7.757 (1.3); 7.753(1.4); 7.737 (3.7); 7.733 (3.7); 7.715 (16.0); 7.695 (5.7); 7.692 (7.7);7.675 (3.5); 7.669 (4.4); 7.665 (3.2); 7.649 (4.6); 7.631 (2.3); 7.628(2.1); 7.608 (0.4); 5.757 (1.4); 3.171 (0.6); 2.678 (0.4); 2.673 (0.5);2.669 (0.4); 2.513 (28.2); 2.509 (56.0); 2.504 (74.5); 2.500 (56.5);2.496 (29.7); 2.335 (0.4); 2.331 (0.5); 2.327 (0.4); 0.146 (0.4); 0.008(3.5); 0.000 (82.0); −0.008 (4.5); −0.150 (0.4). I-20 ¹H-NMR, Solvent[D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.462 (8.7); 8.317 (0.4); 8.048(14.0); 8.027 (16.0); 7.838 (0.8); 7.824 (9.5); 7.821 (9.4); 7.755(15.5); 7.734 (13.2); 7.668 (0.6); 7.647 (0.4); 7.576 (15.3); 7.467(0.5); 3.724 (0.3); 3.713 (0.3); 3.635 (0.5); 3.608 (0.5); 3.536 (0.6);3.510 (0.6); 3.468 (0.6); 3.451 (0.6); 3.435 (0.6); 3.419 (0.6); 3.400(0.6); 3.362 (0.4); 3.343 (0.4); 3.311 (0.3); 3.188 (1.7); 3.171 (1.3);2.822 (0.4); 2.810 (0.4); 2.673 (0.8); 2.508 (89.5); 2.504 (114.0);2.500 (85.6); 2.335 (0.5); 2.331 (0.7); 2.326 (0.5); 0.146 (0.6); 0.007(6.6); 0.000 (114.3); −0.150 (0.6). I-21 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 8.495 (7.3); 7.808 (7.7); 7.804 (7.6);7.699 (13.6); 7.693 (8.7); 7.675 (16.0); 7.636 (5.9); 7.619 (4.0); 7.613(3.3); 7.596 (2.1); 5.757 (1.4); 3.171 (1.4); 2.673 (0.5); 2.508 (64.6);2.504 (79.6); 2.331 (0.5); 0.146 (0.4); 0.000 (67.8); −0.150 (0.4). I-22¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.484 (11.2);8.143 (9.5); 8.137 (10.2); 7.830 (4.5); 7.824 (4.8); 7.801 (16.0); 7.726(10.7); 7.705 (7.6); 7.668 (14.4); 7.635 (0.6); 7.617 (0.7); 7.611(0.7); 7.471 (0.7); 7.464 (0.5); 7.402 (0.7); 7.380 (0.4); 5.757 (0.4);3.187 (0.4); 2.828 (1.0); 2.816 (1.1); 2.673 (0.6); 2.504 (128.2); 2.398(0.6); 2.353 (0.4); 2.331 (1.1); 1.185 (0.6); 0.000 (81.3); −0.150(0.6). I-23 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ =8.494 (2.5); 7.810 (2.6); 7.806 (2.8); 7.707 (3.6); 7.661 (2.8); 7.653(3.0); 7.594 (2.3); 7.572 (2.7); 7.321 (1.4); 7.313 (1.4); 7.299 (1.2);7.291 (1.2); 3.874 (16.0); 3.817 (0.3); 3.188 (0.5); 3.170 (0.7); 2.508(27.5); 2.504 (36.7); 2.499 (28.8); 0.008 (1.6); 0.000 (37.0). I-24¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.489 (10.6);7.988 (0.3); 7.825 (1.3); 7.812 (12.9); 7.809 (13.3); 7.789 (4.5); 7.774(2.7); 7.768 (2.7); 7.753 (1.2); 7.656 (16.0); 7.359 (7.2); 7.336(11.5); 7.314 (6.6); 7.289 (0.3); 7.266 (0.3); 5.757 (2.0); 3.188 (0.9);2.673 (0.5); 2.504 (107.9); 2.500 (88.7); 2.391 (0.3); 2.331 (0.9);0.146 (0.4); 0.000 (86.5); −0.150 (0.5). I-25 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 8.944 (4.5); 8.926 (4.6); 8.426 (6.1);8.317 (0.5); 7.913 (1.4); 7.688 (5.2); 7.684 (6.8); 7.666 (16.0); 7.628(6.8); 7.612 (3.9); 7.606 (5.4); 7.589 (2.0); 7.536 (1.0); 7.518 (0.8);7.514 (0.8); 7.496 (8.8); 7.340 (3.7); 7.335 (4.0); 7.321 (3.6); 7.316(3.9); 6.993 (0.4); 6.974 (0.4); 5.756 (5.6); 3.910 (1.0); 3.785 (0.4);3.187 (5.6); 3.170 (0.6); 2.677 (0.6); 2.672 (0.9); 2.668 (0.7); 2.526(2.1); 2.512 (46.0); 2.508 (94.5); 2.503 (127.6); 2.499 (95.5); 2.494(48.3); 2.335 (0.6); 2.330 (0.8); 2.325 (0.6); 0.146 (0.7); 0.008 (5.7);0.000 (159.7); −0.008 (7.4); −0.150 (0.7) I-26 ¹H-NMR, Solvent[D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.950 (3.9); 8.932 (4.0); 8.422(5.4); 8.136 (5.9); 8.130 (6.5); 7.945 (0.5); 7.940 (0.5); 7.833 (2.5);7.827 (2.7); 7.812 (3.8); 7.806 (4.2); 7.729 (7.1); 7.708 (5.0); 7.488(7.5); 7.340 (3.1); 7.335 (3.5); 7.321 (3.1); 7.316 (3.4); 6.993 (0.4);6.974 (0.4); 3.911 (0.7); 3.789 (0.3); 3.188 (4.5); 3.171 (16.0); 2.678(0.4); 2.673 (0.5); 2.509 (55.1); 2.504 (73.4); 2.500 (57.7); 2.331(0.5); 1.231 (0.6); 0.146 (0.4); 0.007 (3.1); 0.000 (69.5); −0.008(4.9); −0.150 (0.3). I-27 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 8.953 (1.5); 8.935 (1.5); 8.428 (2.1); 7.649 (2.8);7.641 (2.9); 7.590 (2.4); 7.568 (2.8); 7.512 (3.1); 7.343 (1.4); 7.339(1.4); 7.325 (1.4); 7.319 (1.6); 7.317 (1.8); 7.309 (1.4); 7.294 (1.2);7.287 (1.2); 3.869 (16.0); 3.817 (1.2); 3.188 (1.1); 3.170 (0.4); 2.512(13.7); 2.508 (27.5); 2.504 (36.5); 2.499 (27.5); 2.495 (14.2); 0.008(1.5); 0.000 (38.8); −0.008 (2.0). I-28 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 12.426 (0.7); 12.419 (0.7); 8.507 (10.8);7.837 (11.5); 7.682 (16.0); 3.584 (0.4); 3.467 (0.9); 3.450 (1.7); 3.411(49.5); 3.235 (0.6); 3.189 (0.3); 3.170 (0.5); 2.673 (0.6); 2.504(87.0); 2.331 (0.6); 1.074 (0.7); 1.057 (1.3); 1.040 (0.7); 0.000(47.3). I-29 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ =12.271 (2.2); 8.985 (6.6); 8.967 (6.8); 8.438 (9.3); 8.316 (0.4); 7.502(16.0); 7.364 (5.6); 7.359 (6.3); 7.345 (5.7); 7.340 (6.2); 5.756 (1.0);3.910 (0.3); 3.339 (4.6); 3.188 (0.4); 3.170 (3.5); 3.152 (1.2); 3.140(2.6); 3.133 (2.9); 3.121 (5.1); 3.109 (3.3); 3.101 (3.0); 3.089 (1.5);2.677 (0.5); 2.672 (0.7); 2.668 (0.6); 2.508 (79.9); 2.503 (109.9);2.499 (89.8); 2.334 (0.5); 2.330 (0.7); 2.326 (0.6); 1.210 (1.8); 1.190(8.3); 1.178 (10.8); 1.171 (4.4); 1.161 (2.3); 1.149 (4.2); 1.137 (8.2);1.133 (6.8); 1.118 (8.2); 1.113 (6.6); 1.103 (2.1); 1.099 (1.8); 0.146(0.5); 0.008 (4.4); 0.000 (109.5); −0.150 (0.5). I-30 ¹H-NMR, Solvent[D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.314 (11.9); 7.868 (10.9);7.795 (6.7); 7.776 (7.6); 7.579 (11.9); 7.575 (12.3); 7.539 (4.0); 7.519(7.6); 7.489 (7.7); 7.469 (9.8); 7.450 (3.8); 7.438 (0.6); 7.418 (0.5);7.242 (16.0); 3.332 (14.5); 3.222 (0.4); 3.214 (0.4); 3.170 (2.7); 2.673(0.9); 2.504 (144.5); 2.331 (1.0); 1.990 (0.3); 1.353 (0.6); 1.337(1.3); 1.299 (2.8); 1.259 (3.7); 1.250 (2.2); 1.234 (3.2); 1.194 (0.4);1.188 (0.4); 1.176 (0.4); 0.866 (0.4); 0.853 (0.6); 0.835 (0.4); 0.146(0.6); 0.000 (121.7); −0.150 (0.7). I-31 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 12.384 (1.0); 8.498 (8.5); 7.841 (9.1);7.837 (9.3); 7.666 (16.0); 5.756 (0.5); 3.342 (5.5); 3.170 (1.5); 3.156(2.1); 3.149 (2.4); 3.137 (4.1); 3.125 (2.6); 3.117 (2.4); 3.105 (1.2);2.673 (0.5); 2.508 (61.3); 2.504 (81.2); 2.499 (63.8); 2.335 (0.4);2.331 (0.6); 1.225 (1.4); 1.205 (6.7); 1.194 (8.5); 1.185 (3.4); 1.175(1.7); 1.163 (3.3); 1.152 (6.7); 1.147 (5.2); 1.132 (6.7); 1.127 (5.1);1.118 (1.6); 1.113 (1.4); 0.146 (0.4); 0.008 (3.2); 0.000 (80.3); −0.150(0.4). I-32 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ =8.442 (4.9); 7.749 (4.7); 7.745 (4.9); 7.540 (5.5); 3.429 (1.5); 3.411(4.2); 3.392 (4.3); 3.374 (1.8); 3.327 (6.6); 3.170 (0.3); 2.677 (0.3);2.673 (0.4); 2.668 (0.4); 2.508 (50.2); 2.504 (67.2); 2.499 (52.5);2.330 (0.4); 1.352 (0.4); 1.337 (0.4); 1.299 (2.5); 1.259 (3.5); 1.250(7.5); 1.232 (16.0); 1.213 (6.8); 0.008 (2.3); 0.000 (61.5). I-33¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.932(8.7);8.914(8.9); 8.401(12.2); 8.383(12.2); 8.378(12.7); 8.314(1.6);8.109(5.2); 8.105(5.2); 8.088(6.5); 8.084(6.4); 7.934(10.5); 7.913(8.4);7.889(0.5); 7.442(16.0); 7.319(7.6); 7.314(7.7); 7.301(7.4); 7.296(7.5);5.754(2.6); 4.341(0.3); 4.290(0.4); 4.281(0.4); 4.274(0.4); 4.222(0.4);4.210(0.4); 4.172(0.5); 4.159(0.5); 4.027(0.7); 4.004(0.8); 3.910(1.1);3.900(1.1); 3.799(1.4); 3.773(1.5); 3.735(1.5); 3.690(1.6); 3.655(1.6);3.643(1.6); 3.586(1.6); 3.572(1.5); 3.494(1.3); 3.188(0.7); 3.111(0.4);3.081(0.3); 2.676(2.1); 2.672(3.0); 2.667(2.2); 2.525(5.8);2.511(180.6); 2.507(372.5); 2.503(498.0); 2.498(374.2); 2.494(192.2);2.334(2.8); 2.329(3.7); 2.325(2.8); 2.241(0.4); 2.193(0.4); 2.182(0.3);0.146(0.7); 0.008(4.8); 0.000(170.1); −0.008(8.2); −0.150(0.8) I-34¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.949(2.6);8.931(2.9); 8.423(3.7); 8.314(0.4); 7.627(4.8); 7.619(5.3); 7.566(2.5);7.544(3.1); 7.506(3.4); 7.467(0.3); 7.334(2.2); 7.316(2.3); 7.291(1.7);7.284(2.0); 7.269(1.6); 7.262(1.8); 4.157(1.9); 4.140(6.1); 4.123(6.2);4.105(2.2); 3.789(0.4); 3.545(0.4); 3.467(1.1); 3.450(1.7); 3.433(2.1);3.415(2.1); 3.356(3.6); 3.188(0.5); 2.676(0.7); 2.672(1.0); 2.667(0.8);2.507(115.4); 2.502(151.2); 2.498(115.3); 2.334(0.7); 2.329(1.0);2.325(0.7); 1.386(7.7); 1.369(16.0); 1.351(7.5); 1.074(0.7); 1.057(1.3);1.039(0.7); 0.000(44.7); −0.063 (0.4) I-35 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 8.951(3.5); 8.933(3.6); 8.426(5.2);7.637(5.6); 7.630(5.9); 7.590(0.5); 7.567(4.7); 7.545(5.6); 7.528(0.6);7.511(7.4); 7.341(3.1); 7.337(3.1); 7.323(3.1); 7.318(3.1); 7.303(3.1);7.295(3.0); 7.281(2.6); 7.273(2.5); 5.754(2.2); 4.048(4.4); 4.032(8.9);4.016(4.5); 3.996(0.4); 3.979(0.5); 2.672(0.9); 2.507(95.2);2.503(117.9); 2.499(93.4); 2.330(0.7); 1.816(0.6); 1.798(2.5);1.781(5.0); 1.763(5.2); 1.746(2.8); 1.729(0.8); 1.021(8.1); 1.002(16.0);0.984(7.5); 0.959(0.4); 0.000(29.5) I-36 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 8.949(2.9); 8.931(3.0); 8.426(4.2);8.018(5.8); 7.575(12.9); 7.573(12.6); 7.550(0.5); 7.517(6.7);7.342(2.7); 7.337(2.7); 7.324(2.6); 7.319(2.7); 3.478(0.3); 3.469(0.4);3.451(0.5); 3.434(0.5); 3.416(0.4); 3.386(0.4); 2.772(1.9); 2.753(5.8);2.734(6.0); 2.715(2.0); 2.681(0.4); 2.676(0.4); 2.672(0.5); 2.668(0.4);2.664(0.4); 2.526(1.2); 2.508(57.2); 2.503(75.1); 2.499(57.1);2.335(0.4); 2.330(0.5); 2.326(0.4); 1.242(7.5); 1.223(16.0); 1.204(7.4);1.188(0.8); 1.169(0.3); 0.008(0.9); 0.000(24.0); −0.008(1.4) I-37¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.948(1.5);8.929(1.6); 8.427(2.1); 7.749(2.5); 7.727(2.7); 7.694(2.8); 7.686(2.9);7.526(3.0); 7.339(1.3); 7.334(1.3); 7.321(1.3); 7.316(1.3); 7.230(1.3);7.222(1.3); 7.208(1.3); 7.200(1.2); 3.864(16.0); 3.815(0.7); 2.671(0.4);2.507(47.0); 2.502(63.3); 2.498(48.7); 2.329(0.4); 2.324(0.3);0.008(0.7); 0.000(20.4) I-38 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 8.956(1.8); 8.938(1.9); 8.421(2.7); 7.480(4.2);7.447(1.2); 7.439(1.6); 7.433(1.6); 7.425(2.3); 7.402(2.2); 7.379(1.6);7.346(2.4); 7.342(2.4); 7.337(2.1); 7.328(2.5); 7.323(2.5); 7.314(1.1);7.306(0.5); 3.841(16.0); 3.794(0.5); 3.468(0.4); 3.452(0.5); 3.433(0.5);3.415(0.5); 3.315(0.3); 2.503(41.5); 0.000(17.2); −0.006(3.9) I-39¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.819(1.9);8.801(2.0); 8.312(1.8); 8.230(2.7); 7.285(1.4); 7.265(3.3); 7.245(2.8);7.179(2.6); 7.161(1.7); 7.136(2.8); 7.133(2.5); 7.117(2.2); 7.114(1.9);7.094(1.9); 7.089(1.9); 7.076(1.8); 7.071(1.9); 7.039(4.6);3.315(324.7); 2.780(0.4); 2.679(1.3); 2.675(2.5); 2.670(3.5);2.666(2.6); 2.606(0.3); 2.524(9.1); 2.519(14.2); 2.510(184.8);2.506(377.8); 2.501(509.7); 2.497(380.8); 2.492(190.0); 2.337(1.2);2.333(2.5); 2.328(3.5); 2.324(2.7); 2.319(1.9); 2.310(16.0); 2.268(0.6);2.117(0.5); 2.086(0.4); 1.398(1.3); 1.236(0.8); 1.140(1.2); 0.146(1.6);0.008(11.8); 0.000(354.9); −0.009(13.4); −0.150(1.6) I-40 ¹H-NMR,Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.943(3.3); 8.925(3.4);8.427(4.7); 8.314(0.4); 7.665(0.6); 7.543(1.4); 7.522(3.8); 7.505(8.2);7.489(4.8); 7.471(1.8); 7.426(0.4); 7.403(0.4); 7.384(3.6); 7.381(3.6);7.365(3.1); 7.362(3.0); 7.335(2.9); 7.330(3.0); 7.317(2.8); 7.312(2.9);3.468(1.0); 3.450(2.0); 3.433(2.2); 3.415(1.9); 3.345(6.5); 3.220(0.4);3.187(0.6); 3.030(2.0); 3.012(6.0); 2.994(6.2); 2.975(2.4); 2.956(0.6);2.946(0.5); 2.937(0.4); 2.927(0.5); 2.671(1.2); 2.667(1.0);2.507(130.3); 2.502(168.1); 2.498(130.9); 2.334(0.8); 2.329(1.0);2.325(0.8); 1.279(7.5); 1.261(16.0); 1.242(7.3); 1.190(0.4); 1.172(0.6);1.121(0.8); 1.074(1.3); 1.056(2.5); 1.039(1.2); 0.146(0.4); 0.008(4.7);0.000(92.5); −0.149 (0.4) I-41 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 8.944(1.9); 8.925(1.9); 8.429(2.5); 8.313(0.6);7.636(0.9); 7.590(1.1); 7.569(2.1); 7.539(1.4); 7.520(2.6); 7.511(2.7);7.501(1.5); 7.486(0.6); 7.464(0.4); 7.445(0.5); 7.424(0.4); 7.407(2.2);7.387(1.6); 7.377(0.6); 7.357(0.4); 7.328(1.5); 7.310(1.4); 3.714(0.5);3.697(1.0); 3.681(1.3); 3.665(1.0); 3.649(0.5); 3.622(0.3); 3.606(0.4);3.589(0.3); 3.467(0.5); 3.449(1.1); 3.432(1.3); 3.414(1.0); 3.331(60.2);3.187(0.4); 2.675(1.5); 2.670(1.9); 2.666(1.6); 2.506(222.1);2.502(288.1); 2.497(225.0); 2.333(1.4); 2.328(1.8); 2.324(1.4);1.282(2.9); 1.265(3.2); 1.250(16.0); 1.234(15.6); 1.197(0.3);1.123(0.6); 1.073(0.9); 1.056(1.6); 1.038(0.8); 0.146(0.7);0.000(147.6); −0.150 (0.7) I-42 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 8.841(1.5); 8.822(1.5); 8.268(1.7); 7.144(1.7);7.128(1.9); 6.449(0.7); 6.430(0.7); 6.223(0.5); 6.201(0.7); 6.177(0.5);3.639(0.5); 3.624(0.7); 3.610(0.5); 3.316(8.3); 2.675(0.5); 2.671(0.6);2.666(0.5); 2.524(1.7); 2.511(35.8); 2.506(72.0); 2.502(96.4);2.497(71.8); 2.493(36.0); 2.333(0.5); 2.328(0.7); 2.324(0.5);1.398(1.9); 1.236(0.9); 1.171(16.0); 1.156(15.9); 1.141(0.6);0.008(2.1); 0.000(61.9); −0.008 (2.6) I-43 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 8.951(6.3); 8.933(6.4); 8.427(9.1);8.314(0.4); 7.937(0.6); 7.741(2.0); 7.727(2.4); 7.720(4.4); 7.707(4.5);7.700(3.0); 7.686(2.6); 7.539(7.5); 7.519(6.2); 7.496(16.0); 7.471(4.0);7.468(4.4); 7.446(2.9); 7.345(5.6); 7.340(5.7); 7.326(5.4); 7.321(5.5);5.754(4.3); 3.910(0.5); 3.753(0.6); 3.700(0.3); 3.619(0.4); 3.602(0.4);3.562(0.4); 3.538(0.4); 3.525(0.4); 3.483(0.4); 3.432(0.4); 3.420(0.6);3.303(0.3); 3.188(0.7); 2.676(1.0); 2.672(1.3); 2.668(1.0);2.507(141.7); 2.503(179.6); 2.499(136.2); 2.334(0.9); 2.330(1.1);2.325(0.9); 0.146(0.5); 0.008(5.8); 0.000(100.7); −0.150(0.5) I-44¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.492(5.7);8.317(0.3); 7.804(5.8); 7.696(5.8); 7.637(5.9); 7.629(6.0); 7.567(4.0);7.545(4.6); 7.292(2.6); 7.285(2.7); 7.270(2.3); 7.263(2.2); 4.161(2.4);4.144(7.1); 4.127(7.2); 4.109(2.4); 3.389(5.9); 3.187(0.5); 3.139(0.4);2.672(1.3); 2.503(182.1); 2.330(1.2); 1.390(7.9); 1.373(16.0);1.355(7.8); 0.146(0.4); 0.000(81.2); −0.150(0.4) I-45 ¹H-NMR, Solvent[D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.488(6.0); 8.317(0.5);7.800(6.1); 7.683(5.5); 7.642(6.3); 7.635(6.0); 7.603(1.4); 7.558(3.9);7.537(4.4); 7.509(0.7); 7.467(0.7); 7.461(0.6); 7.292(3.0); 7.286(2.9);7.270(2.6); 7.184(0.3); 4.102(0.4); 4.048(5.3); 4.032(9.3); 4.016(5.0);3.995(1.1); 3.978(1.3); 3.962(0.8); 3.934(0.4); 3.913(0.4); 3.868(0.4);3.844(0.5); 3.780(0.6); 3.764(0.6); 3.665(0.9); 3.356(141.1);3.162(1.4); 3.024(0.6); 2.997(0.5); 2.992(0.5); 2.987(0.5); 2.954(0.5);2.927(0.4); 2.898(0.4); 2.884(0.5); 2.879(0.4); 2.824(0.6); 2.798(0.6);2.788(0.6); 2.673(3.0); 2.503(352.2); 2.330(2.5); 1.818(1.0);1.801(3.1); 1.783(5.8); 1.766(6.0); 1.749(3.6); 1.732(1.4); 1.073(0.5);1.056(1.0); 1.023(8.7); 1.005(16.0); 0.987(8.0); 0.958(1.0); 0.147(0.4);0.000(56.5); −0.149(0.3) I-46 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 8.217(5.3); 8.214(5.7); 8.198(5.8); 8.195(6.0);8.114(10.2); 8.109(10.5); 7.752(1.7); 7.734(4.7); 7.717(5.0);7.714(5.0); 7.691(9.1); 7.674(4.3); 7.665(4.7); 7.642(14.6);7.637(10.9); 7.628(3.1); 7.423(16.0); 5.759(1.4); 3.426(1.2);2.674(0.8); 2.508(85.6); 2.505(105.9); 2.331(0.7); 0.000(11.3) I-47¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.317(1.3);8.121(14.7); 8.115(15.2); 8.089(15.8); 8.084(16.0); 7.944(0.4);7.938(0.4); 7.807(5.0); 7.801(5.4); 7.785(7.4); 7.779(7.3); 7.706(14.9);7.684(9.4); 7.614(13.3); 7.608(13.2); 7.346(14.6); 5.758(3.4);4.038(0.4); 4.036(0.4); 4.028(0.4); 3.979(0.5); 3.964(0.5); 3.911(0.9);3.834(0.9); 3.767(1.2); 3.749(1.3); 3.699(1.8); 3.443(11.8); 3.187(2.1);3.138(1.4); 3.110(1.3); 3.064(0.9); 2.944(0.5); 2.933(0.4); 2.867(0.3);2.676(2.8); 2.672(4.0); 2.668(2.9); 2.525(8.0); 2.507(470.0);2.503(614.4); 2.499(452.7); 2.377(0.7); 2.366(0.7); 2.334(3.4);2.330(4.4); 2.325(3.4); 2.275(0.5); 2.200(0.4); 2.180(0.4); 2.161(0.3);0.146(0.3); 0.008(2.4); 0.000(77.5); −0.008(3.3); −0.149(0.4) I-48¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.114(7.9);8.109(8.2); 7.697(5.7); 7.693(6.8); 7.675(16.0); 7.637(11.2);7.620(4.1); 7.614(3.2); 7.598(2.0); 7.413(11.5); 5.759(2.4); 3.912(0.5);3.695(0.3); 3.683(0.3); 3.644(0.4); 3.632(0.4); 3.617(0.4); 3.573(0.4);3.562(0.4); 3.537(0.4); 3.491(0.4); 3.411(0.3); 2.673(0.7); 2.508(73.9);2.505(92.5); 2.331(0.6); 0.000(10.2) I-49 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 8.113(2.9); 8.108(2.9); 7.651(3.0);7.642(4.5); 7.636(2.8); 7.595(2.3); 7.573(2.7); 7.418(4.0); 7.320(1.4);7.313(1.4); 7.298(1.2); 7.291(1.2); 3.871(16.0); 3.724(0.5); 3.450(0.5);3.432(0.6); 3.415(0.5); 3.392(0.5); 3.375(0.4); 3.360(0.4); 2.508(32.3);2.504(41.1); 2.500(30.4); 0.000(3.0) I-50 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 9.353(1.8); 8.057(1.3); 8.034(1.5);7.648(2.8); 7.640(2.9); 7.595(2.3); 7.580(1.4); 7.573(3.1); 7.556(1.2);7.553(1.3); 7.414(2.9); 7.319(1.4); 7.311(1.3); 7.297(1.2); 7.289(1.1);3.869(16.0); 3.816(0.5); 3.723(0.6); 3.467(0.8); 3.449(1.3); 3.432(1.6);3.414(1.5); 3.395(1.5); 2.677(0.3); 2.672(0.4); 2.668(0.3); 2.526(1.1);2.521(1.6); 2.512(23.4); 2.508(48.0); 2.503(63.1); 2.499(45.5);2.494(21.7); 2.330(0.4); 1.074(0.5); 1.056(1.1); 1.038(0.5); 0.000(4.6)I-51 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ =9.343(10.6); 8.317(0.8); 8.131(13.9); 8.125(14.7); 8.047(7.5);8.023(8.3); 7.943(0.8); 7.938(0.8); 7.827(5.6); 7.820(5.5); 7.805(8.7);7.799(9.5); 7.725(16.0); 7.712(1.6); 7.704(11.9); 7.681(0.3);7.613(0.5); 7.607(0.7); 7.570(7.2); 7.567(7.3); 7.546(6.5); 7.543(6.7);7.471(0.4); 7.464(0.4); 7.402(0.7); 7.377(15.8); 4.078(0.4); 4.022(0.4);3.948(0.6); 3.912(0.9); 3.810(1.0); 3.800(1.1); 3.671(2.1); 3.491(4.2);3.467(5.1); 3.449(7.1); 3.432(7.0); 3.415(4.6); 3.301(2.0); 3.187(1.5);3.137(0.9); 3.110(0.8); 3.066(0.6); 3.027(0.5); 2.994(0.5); 2.961(0.4);2.944(0.4); 2.920(0.3); 2.910(0.3); 2.796(0.4); 2.784(0.3); 2.772(0.3);2.677(1.6); 2.672(2.2); 2.668(1.7); 2.526(4.0); 2.512(116.4);2.508(242.8); 2.503(325.9); 2.499(244.8); 2.495(126.3); 2.378(0.5);2.334(1.8); 2.330(2.4); 2.326(1.9); 1.073(3.2); 1.056(6.3); 1.038(3.1);0.008(0.6); 0.000(20.7); −0.009 (1.0) I-52 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 9.332(6.6); 8.318(0.3); 8.056(4.5);8.032(5.0); 7.691(5.5); 7.687(6.8); 7.669(16.0); 7.631(6.1); 7.614(4.0);7.608(3.4); 7.591(2.2); 7.578(4.4); 7.575(4.5); 7.554(3.9); 7.551(4.1);7.400(9.2); 3.467(1.9); 3.450(3.3); 3.432(3.3); 3.415(1.8); 3.188(0.4);2.677(0.8); 2.673(1.1); 2.668(0.8); 2.508(121.4); 2.504(158.5);2.499(119.6); 2.335(0.8); 2.330(1.1); 2.326(0.9); 1.074(2.2);1.056(4.3); 1.039(2.1); 0.146(0.4); 0.008(3.2); 0.000(79.6);−0.008(3.9); −0.150(0.4) I-53 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 8.319(0.4); 8.184(6.5); 8.161(7.0); 8.141(10.6);8.135(10.8); 7.944(0.7); 7.939(0.7); 7.835(3.9); 7.829(3.9); 7.814(5.9);7.808(6.0); 7.730(16.0); 7.713(8.8); 7.709(9.7); 7.522(11.1);7.477(4.5); 7.455(5.4); 7.436(3.7); 5.759(0.3); 3.915(1.2); 3.808(0.6);3.642(0.7); 3.603(0.7); 3.528(0.7); 3.498(0.7); 3.468(0.7); 3.450(0.8);3.433(0.7); 3.415(0.6); 3.314(0.5); 3.217(0.3); 3.187(0.4); 2.673(1.4);2.508(170.4); 2.504(215.9); 2.500(164.9); 2.434(0.4); 2.335(1.1);2.331(1.5); 2.327(1.2); 1.056(0.4); 0.146(0.5); 0.000(108.8);−0.150(0.5) I-54 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ= 9.450(5.2); 9.447(5.4); 7.941(0.5); 7.930(0.4); 7.856(6.4);7.853(6.7); 7.251(6.8); 6.975(0.3); 5.758(0.7); 5.666(0.3); 5.584(0.5);5.556(0.5); 5.539(0.5); 5.523(0.5); 5.516(0.5); 5.507(0.5); 5.390(0.3);3.930(0.8); 3.217(1.6); 3.187(2.4); 2.795(0.5); 2.783(0.7); 2.677(0.3);2.673(0.5); 2.669(0.4); 2.526(1.1); 2.513(29.2); 2.508(59.6);2.504(79.9); 2.499(60.9); 2.495(31.5); 2.335(0.4); 2.331(0.6);2.326(0.4); 2.060(7.3); 2.013(16.0); 1.986(0.9); 1.965(8.2); 1.939(1.6);1.892(0.9); 1.233(0.5); 0.008(2.4); 0.000(70.7); −0.008(3.0);−0.150(0.3) I-55 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ= 9.446(5.0); 9.444(5.1); 8.232(0.7); 8.217(1.1); 8.213(1.1);8.198(0.7); 7.928(0.5); 7.776(6.4); 7.774(6.4); 6.995(8.6); 6.973(1.4);6.237(0.6); 6.175(0.4); 3.930(1.3); 3.217(1.6); 3.186(16.0); 2.796(0.8);2.785(1.1); 2.773(0.5); 2.678(0.4); 2.673(0.5); 2.669(0.4); 2.509(58.3);2.504(75.8); 2.500(57.3); 2.336(0.4); 2.331(0.5); 2.327(0.4);2.209(0.7); 1.233(0.5); 0.839(0.4); 0.008(2.5); 0.000(58.2) I-56 ¹H-NMR,Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.383(9.3);8.379(10.0); 8.314(0.6); 8.211(0.5); 8.103(4.2); 8.082(16.0);8.077(13.9); 8.011(0.3); 7.931(8.0); 7.910(6.4); 7.889(1.1); 7.606(9.2);7.601(9.7); 7.339(13.9); 5.755(12.2); 4.255(0.3); 4.102(0.3);4.072(0.4); 4.036(0.4); 3.910(0.6); 2.672(2.0); 2.667(1.6);2.507(232.8); 2.503(307.9); 2.498(237.4); 2.329(2.1); 2.325(1.6);2.086(0.9); 0.146(1.6); 0.008(13.3); 0.000(335.9); −0.150(1.6) I-57¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.109(5.9);8.103(6.0); 7.634(6.9); 7.630(9.5); 7.623(6.5); 7.571(4.9); 7.549(5.7);7.414(8.5); 7.297(2.9); 7.289(2.8); 7.275(2.5); 7.267(2.4); 4.160(2.2);4.143(7.1); 4.126(7.1); 4.108(2.3); 3.468(0.4); 3.451(0.8); 3.433(0.8);3.416(0.4); 2.677(0.5); 2.672(0.7); 2.667(0.5); 2.525(2.3); 2.507(70.9);2.503(92.7); 2.499(69.3); 2.334(0.4); 2.330(0.6); 2.326(0.4);1.388(7.7); 1.370(16.0); 1.353(7.5); 1.074(0.5); 1.057(1.0); 1.039(0.5);0.146(0.5); 0.008(4.1); 0.000(94.2); −0.008(4.4); −0.150 (0.5) I-58¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.108(5.2);8.103(5.3); 7.638(6.2); 7.633(6.3); 7.630(8.5); 7.567(4.2); 7.545(4.9);7.412(7.0); 7.304(2.5); 7.296(2.4); 7.282(2.1); 7.274(2.0); 4.048(3.9);4.032(8.1); 4.016(4.0); 3.910(0.6); 3.552(0.3); 3.544(0.4); 3.512(0.4);3.472(0.5); 3.450(0.6); 3.433(0.6); 3.415(0.5); 3.404(0.5); 3.391(0.5);3.355(0.4); 2.676(0.6); 2.671(0.8); 2.667(0.6); 2.563(0.3); 2.524(2.5);2.511(44.3); 2.507(87.8); 2.502(116.5); 2.498(87.0); 2.333(0.5);2.329(0.7); 2.324(0.5); 1.816(0.5); 1.798(2.1); 1.781(4.3); 1.763(4.5);1.746(2.3); 1.728(0.6); 1.021(7.8); 1.002(16.0); 0.984(7.2); 0.146(0.7);0.008(5.3); 0.000(136.6); −0.008 (6.4); −0.150(0.6) I-59 ¹H-NMR, Solvent[D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.110(6.1); 8.106(6.1);8.022(7.1); 7.635(5.8); 7.630(5.6); 7.578(15.6); 7.551(0.7); 7.526(0.3);7.426(9.1); 3.911(0.4); 2.773(2.3); 2.754(6.8); 2.735(6.9); 2.716(2.5);2.673(0.7); 2.503(82.6); 2.330(0.5); 1.244(8.0); 1.225(16.0);1.206(8.0); 1.188(0.9); 1.169(0.4); 0.146(0.4); 0.000(71.1); −0.150(0.4)I-60 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ =8.106(3.0); 8.101(3.0); 7.943(3.1); 7.941(3.1); 7.632(2.9); 7.627(2.8);7.611(0.6); 7.591(6.9); 7.565(0.3); 7.406(4.1); 5.754(0.4); 2.672(0.4);2.574(16.0); 2.503(49.8); 0.000(37.7) I-61 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 8.116(6.3); 8.111(6.6); 7.634(6.2);7.629(6.2); 7.552(1.4); 7.532(4.2); 7.513(4.9); 7.498(5.2); 7.480(2.0);7.447(0.5); 7.427(9.7); 7.391(4.1); 7.375(3.1); 7.372(3.2); 5.754(6.1);3.532(0.3); 3.415(0.7); 3.036(2.1); 3.018(6.6); 3.000(6.9); 2.981(2.5);2.962(0.5); 2.673(0.6); 2.507(70.3); 2.503(91.6); 2.499(72.0);2.330(0.6); 1.285(7.6); 1.267(16.0); 1.248(7.4); 1.203(0.4); 1.185(0.7);1.166(0.3); 1.121(0.5); 0.146(0.4); 0.000(78.0); −0.150(0.4) I-62¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.495(5.1);8.031(6.3); 7.808(5.6); 7.804(5.2); 7.718(7.6); 7.580(13.9); 3.468(0.4);3.464(0.3); 3.451(0.5); 3.434(0.4); 2.777(2.1); 2.758(6.3); 2.739(6.5);2.721(2.2); 2.672(0.7); 2.508(72.2); 2.503(89.0); 2.500(66.1);2.330(0.5); 1.248(7.8); 1.229(16.0); 1.211(7.4); 0.146(0.4);0.000(75.6); −0.149(0.4) I-63 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 8.495(5.0); 8.314(0.6); 7.799(5.2); 7.795(5.0);7.704(4.9); 7.545(1.1); 7.525(3.3); 7.506(4.0); 7.494(4.3); 7.475(1.6);7.388(3.3); 7.370(2.7); 3.584(0.4); 3.467(2.0); 3.450(3.8); 3.432(4.5);3.414(4.3); 3.377(6.0); 3.188(0.6); 3.173(0.3); 3.033(2.0); 3.015(6.0);2.997(6.1); 2.979(2.3); 2.964(0.6); 2.675(1.5); 2.671(2.0); 2.667(1.5);2.557(0.5); 2.506(225.3); 2.502(288.0); 2.498(213.5); 2.333(1.3);2.329(1.8); 2.324(1.4); 1.286(7.5); 1.268(16.0); 1.250(7.3); 1.207(0.5);1.189(0.8); 1.170(0.4); 1.120(1.0); 1.074(2.0); 1.056(3.9); 1.039(1.9);0.146(1.2); 0.008(11.4); 0.000(254.1); −0.041(0.3); −0.150(1.3) I-64¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.507(3.4);7.810(3.6); 7.726(4.4); 7.637(0.4); 7.609(1.5); 7.589(2.7); 7.556(1.7);7.537(2.6); 7.517(1.3); 7.425(2.6); 7.406(2.0); 5.755(1.5); 3.729(0.5);3.712(1.2); 3.696(1.6); 3.679(1.3); 3.663(0.6); 3.468(1.2); 3.451(1.9);3.433(2.1); 3.415(1.9); 3.272(0.4); 2.672(0.5); 2.503(83.0); 2.330(0.6);1.296(1.1); 1.282(1.0); 1.257(16.0); 1.240(15.8); 1.212(0.5);1.196(0.4); 1.124(0.6); 1.074(0.8); 1.057(1.4); 1.039(0.7); 0.000(57.8)I-65 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ =8.490(10.5); 8.314(0.4); 7.805(11.1); 7.802(11.2); 7.741(2.0);7.727(2.3); 7.720(4.5); 7.707(4.7); 7.700(3.2); 7.678(16.0); 7.540(7.8);7.520(6.4); 7.496(3.8); 7.469(4.5); 7.447(3.2); 5.755(1.1); 3.468(0.4);3.451(0.9); 3.433(0.9); 3.416(0.5); 2.819(0.5); 2.807(0.5); 2.672(1.1);2.508(139.7); 2.503(183.9); 2.499(141.7); 2.334(1.0); 2.330(1.3);1.075(0.7); 1.057(1.3); 1.040(0.7); 0.146(0.8); 0.008(6.5);0.000(165.8); −0.150(0.9) I-66 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 8.106(3.1); 8.101(3.2); 7.633(3.0); 7.627(3.0);7.412(0.6); 7.398(5.5); 7.374(1.1); 7.353(0.6); 6.682(1.8); 6.659(1.7);6.429(1.0); 6.409(1.0); 6.401(1.1); 6.381(1.0); 3.809(0.4); 3.794(0.9);3.778(1.3); 3.763(0.9); 3.747(0.4); 2.507(30.2); 2.503(39.9);2.499(30.0); 1.397(1.7); 1.238(16.0); 1.223(15.0); 0.008(1.5);0.000(38.9); −0.008(1.8) I-67 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 8.109(10.1); 8.104(10.4); 7.937(0.4); 7.746(1.7);7.733(1.9); 7.726(3.8); 7.712(3.9); 7.705(2.6); 7.691(2.3); 7.637(9.6);7.632(9.5); 7.544(6.3); 7.524(5.2); 7.500(3.0); 7.476(3.2); 7.473(3.6);7.451(2.6); 7.398(16.0); 5.754(2.1); 2.677(0.4); 2.673(0.6); 2.668(0.4);2.526(0.8); 2.512(40.9); 2.508(84.3); 2.504(113.5); 2.499(86.9);2.335(0.7); 2.330(0.9); 2.326(0.7); 0.146(0.5); 0.008(3.9);0.000(123.8); −0.008(7.9); −0.037(0.5); −0.052(0.4); −0.150(0.7) I-68¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.095(2.5);8.090(2.6); 7.629(2.2); 7.624(2.2); 7.445(1.1); 7.437(1.3); 7.431(1.3);7.423(1.3); 7.414(0.7); 7.391(1.6); 7.367(1.2); 7.351(3.0); 7.334(0.7);7.325(1.2); 7.316(0.7); 7.302(0.6); 7.293(0.3); 3.839(16.0); 3.793(0.6);3.401(1.1); 2.671(0.8); 2.506(95.4); 2.502(125.8); 2.498(95.5);2.329(0.8); 0.008(2.1); 0.000(59.1) I-69 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 8.113(2.9); 8.108(3.0); 7.754(2.6);7.732(2.8); 7.698(2.9); 7.690(3.1); 7.635(2.7); 7.630(2.8); 7.444(4.4);7.237(1.4); 7.229(1.4); 7.215(1.3); 7.207(1.3); 3.867(16.0); 3.816(0.6);3.451(0.5); 3.434(0.5); 2.525(0.4); 2.508(24.3); 2.503(32.4);2.499(24.8); 1.075(0.4); 1.057(0.8); 1.040(0.4); 0.008(0.6); 0.000(17.3)I-70 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ =8.493(2.4); 7.802(2.6); 7.798(2.5); 7.750(2.3); 7.728(3.6); 7.724(3.5);7.705(2.9); 7.697(2.9); 7.232(1.3); 7.224(1.2); 7.210(1.2); 7.202(1.1);3.868(16.0); 3.815(0.4); 3.510(0.3); 3.468(0.5); 3.450(0.7); 3.433(0.7);3.415(0.4); 2.676(0.4); 2.672(0.5); 2.507(55.4); 2.502(71.2);2.498(52.8); 2.333(0.4); 2.329(0.5); 1.074(0.3); 1.057(0.7); 1.039(0.3);0.008(1.4); 0.000(34.9) I-71 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 8.495(13.7); 8.314(0.9); 7.802(15.6); 7.755(0.8);7.742(2.2); 7.724(2.0); 7.707(16.0); 7.662(0.5); 7.636(0.4); 7.576(4.5);7.555(10.3); 7.535(7.6); 7.517(1.1); 7.508(1.4); 7.488(0.8); 7.478(0.6);7.448(10.1); 7.427(7.2); 7.389(10.5); 7.370(8.4); 7.246(1.8);7.226(1.5); 3.796(0.4); 3.723(0.5); 3.467(4.4); 3.450(6.4); 3.432(6.9);3.415(5.7); 3.187(0.8); 3.181(0.7); 3.107(0.4); 3.090(0.5); 3.073(0.4);3.062(0.4); 3.027(0.3); 3.020(0.3); 3.000(0.5); 2.983(0.5); 2.962(0.5);2.942(0.5); 2.926(0.4); 2.777(3.3); 2.730(0.6); 2.671(3.1);2.506(348.8); 2.502(438.0); 2.486(82.2); 2.452(10.9); 2.419(1.1);2.329(2.8); 2.310(0.4); 1.411(0.3); 1.296(2.2); 1.258(0.3); 1.236(0.3);1.118(2.0); 1.100(0.4); 1.074(2.0); 1.056(4.0); 1.039(2.0); 0.851(0.4);0.832(0.6); 0.643(0.6); 0.146(0.9); 0.000(176.5); −0.150(1.0) I-72¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.475(10.5);8.400(9.4); 8.396(9.8); 8.126(4.4); 8.121(4.4); 8.105(5.3); 8.100(5.2);7.948(8.4); 7.927(6.7); 7.891(0.4); 7.789(11.5); 7.785(10.7);7.652(16.0); 5.755(4.7); 2.674(0.8); 2.670(0.6); 2.509(89.5);2.505(118.2); 2.501(91.8); 2.336(0.5); 2.332(0.7); 2.328(0.6);0.008(2.4); 0.000(62.1); −0.150(0.3) I-73 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 8.933(8.1); 8.914(8.2); 8.409(12.0);8.403(14.4); 8.397(12.1); 8.314(0.6); 8.119(7.6); 8.098(10.6);7.998(6.5); 7.993(6.5); 7.977(4.7); 7.972(4.6); 7.863(0.4); 7.476(16.0);7.326(7.0); 7.321(7.1); 7.307(6.8); 7.302(6.8); 5.755(0.4); 4.202(0.3);4.172(0.3); 4.146(0.3); 4.131(0.3); 4.119(0.3); 4.098(0.4); 4.078(0.4);4.061(0.4); 4.055(0.4); 4.042(0.4); 4.036(0.4); 4.029(0.4); 4.018(0.4);3.993(0.4); 3.969(0.4); 3.921(0.4); 3.910(0.4); 3.874(0.4); 3.851(0.4);3.844(0.4); 3.826(0.4); 3.816(0.4); 3.804(0.4); 3.797(0.4); 3.773(0.4);3.755(0.3); 3.742(0.3); 2.677(1.1); 2.672(1.6); 2.668(1.1);2.508(214.1); 2.503(282.4); 2.499(213.8); 2.334(1.6); 2.330(2.1);2.326(1.7); 0.146(0.6); 0.008(5.0); 0.000(142.6); −0.007(9.3);−0.045(0.4); −0.150(0.8) I-74 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 8.486(2.6); 7.812(2.8); 7.808(2.7); 7.663(4.2);7.461(1.1); 7.453(1.5); 7.447(1.4); 7.439(1.4); 7.431(0.9); 7.408(2.0);7.384(1.4); 7.351(0.8); 7.342(1.4); 7.334(0.9); 7.320(0.8); 7.311(0.4);3.847(16.0); 3.469(1.4); 3.452(4.0); 3.434(4.1); 3.417(1.4);2.508(24.8); 2.504(31.5); 2.500(24.5); 1.075(4.0); 1.058(7.8);1.040(3.9); 0.000(14.3) I-75 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 8.314(0.4); 8.089(4.0); 8.084(4.1); 8.051(0.5);8.046(0.6); 8.008(1.0); 8.003(1.1); 7.894(3.7); 7.869(0.4); 7.633(3.8);7.628(3.9); 7.611(1.0); 7.605(1.0); 7.454(1.6); 7.435(2.1); 7.340(5.2);7.327(3.2); 7.307(2.5); 7.241(0.9); 7.198(1.8); 4.850(0.4); 4.841(0.4);4.795(0.4); 4.779(0.4); 3.432(0.4); 3.341(8.7); 3.022(0.4); 3.003(0.4);2.718(1.3); 2.699(4.1); 2.680(4.5); 2.661(1.9); 2.639(0.4); 2.621(0.4);2.585(16.0); 2.536(1.8); 2.506(140.2); 2.502(179.5); 2.498(138.6);2.382(1.4); 2.329(1.2); 1.228(5.6); 1.209(11.7); 1.190(5.5); 1.160(0.5);1.141(0.9); 1.122(0.4); 0.146(0.9); 0.000(172.1); −0.150(0.9) I-76¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.314(0.6);8.126(0.5); 8.111(12.1); 8.106(11.7); 7.682(0.4); 7.631(11.5);7.626(10.9); 7.588(0.3); 7.575(3.8); 7.555(8.7); 7.535(6.4); 7.523(1.4);7.514(1.1); 7.506(0.7); 7.500(0.5); 7.485(0.4); 7.480(0.4); 7.472(0.4);7.445(8.8); 7.432(3.2); 7.418(16.0); 7.389(8.1); 7.370(6.6); 7.262(0.4);7.243(0.7); 7.222(0.7); 5.754(3.1); 3.911(1.2); 3.719(0.3); 3.622(0.6);3.613(0.6); 3.605(0.7); 3.468(3.2); 3.450(6.6); 3.433(6.7); 3.415(3.2);3.257(0.5); 3.187(0.4); 2.981(0.4); 2.770(4.2); 2.676(1.4); 2.672(1.9);2.667(1.5); 2.622(0.6); 2.507(200.9); 2.503(263.6); 2.498(198.7);2.484(50.9); 2.451(3.7); 2.426(0.4); 2.413(0.4); 2.333(1.2); 2.329(1.6);2.325(1.2); 1.292(2.3); 1.234(0.7); 1.118(0.9); 1.074(5.0); 1.057(9.9);1.039(4.9); 0.855(0.4); 0.850(0.4); 0.831(0.6); 0.146(1.3); 0.008(10.9);0.000(273.2); −0.008(14.3); −0.150(1.3) I-77 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 8.473(4.4); 8.374(0.4); 7.914(4.3);7.889(0.6); 7.802(4.9); 7.766(0.5); 7.645(6.4); 7.526(0.3); 7.480(0.9);7.463(2.2); 7.445(2.6); 7.364(0.5); 7.336(3.3); 7.316(2.5); 3.474(0.3);3.455(0.4); 3.437(0.4); 3.420(0.3); 3.036(0.4); 3.017(0.4); 2.725(1.7);2.706(4.3); 2.687(4.5); 2.669(1.9); 2.637(0.5); 2.598(16.0);2.506(30.8); 2.390(1.5); 1.234(5.4); 1.216(10.3); 1.197(5.1);1.168(0.6); 1.150(0.9); 1.131(0.5); 0.000(9.3) I-78 ¹H-NMR, Solvent[D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.892(0.8); 8.874(0.8);8.322(1.0); 7.824(1.2); 7.689(4.2); 7.664(0.4); 7.337(0.9); 7.329(1.8);7.325(2.0); 7.305(4.7); 7.297(8.0); 7.275(4.9); 7.255(2.6); 7.213(1.1);3.311(10.9); 2.954(0.4); 2.935(0.4); 2.683(0.6); 2.665(2.0); 2.659(2.1);2.640(5.1); 2.621(5.0); 2.602(1.7); 2.550(6.7); 2.538(20.3);2.505(46.4); 2.501(60.9); 2.497(46.5); 2.348(0.5); 2.327(1.9);2.085(1.1); 1.398(1.6); 1.353(0.3); 1.336(0.8); 1.259(0.5); 1.250(1.1);1.236(2.6); 1.219(2.7); 1.208(1.1); 1.200(11.5); 1.190(1.9);1.182(16.0); 1.163(6.6); 1.101(0.4); 0.008(0.5); 0.000(11.0)

Intermediates of Compounds of General Formula (II):

TABLE 4 (II)

Example R¹ n Remarks Code BCS II-1 4-Cl, 2 NMR 6-CF₃ II-2 5-CF₃, 2 NMR7-Cl II-3 5-CF₃ 1 NMR II-4 5-Cl, 2 NMR MKH24284-1-1 BCS-CY75362 neu 7-ClII-5 6-CF₃ 1 NMR MKH24306-1-1 BCS-CY80142 neu II-6 7-CF₃ 1 NMRMKH24442-1-1 BCS-CY80139 neu Z = O and R² = H ¹H-NMR data of compoundsof general formula (II):

TABLE 5 Example NMR data II-1 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 13.593 (1.6); 9.518 (9.9); 9.516 (9.9); 9.434 (0.7);8.316 (0.9); 8.006 (0.6); 7.983 (0.6); 7.895 (12.7); 7.893 (12.9); 7.542(0.5); 7.538 (0.5); 7.518 (0.5); 7.514 (0.5); 7.240 (16.0); 7.219 (1.3);3.860 (0.6); 3.411 (0.5); 3.322 (104.5); 2.676 (2.2); 2.671 (3.0); 2.667(2.2); 2.524 (8.0); 2.511 (162.5); 2.507 (325.3); 2.502 (433.9); 2.498(320.4); 2.493 (156.8); 2.333 (2.1); 2.329 (2.9); 2.324 (2.1); 0.146(0.9); 0.008 (7.2); 0.000 (210.4); −0.008 (7.1); −0.150 (0.9) II-2¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 8.535 (1.2);8.420 (7.8); 7.939 (1.4); 7.934 (1.5); 7.783 (9.0); 7.778 (9.4); 7.480(16.0); 5.758 (0.6); 2.676 (0.4); 2.529 (1.1); 2.515 (23.3); 2.511(47.4); 2.507 (63.9); 2.502 (49.8); 2.498 (27.4); 2.333 (0.4); 1.912(0.4); 1.230 (0.6); 0.146 (0.3); 0.008 (2.8); 0.000 (73.5); −0.150 (0.3)II-3 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer: 399.95 MHz: δ = 13.387(0.4); 13.332 (0.8); 13.258 (0.3); 8.986 (6.5); 8.967 (6.7); 8.383(0.3); 8.361 (9.3); 7.379 (0.5); 7.320 (16.0); 7.313 (7.8); 7.308 (7.1);7.294 (6.1); 7.289 (6.2); 6.485 (0.3); 6.482 (0.3); 4.040 (0.5); 4.022(0.5); 3.913 (2.1); 3.883 (0.6); 3.453 (0.6); 3.435 (0.7); 3.386 (0.9);3.372 (0.9); 2.676 (0.4); 2.672 (0.4); 2.548 (0.4); 2.511 (48.1); 2.507(64.2); 2.502 (50.7); 2.338 (0.3); 2.334 (0.4); 2.329 (0.4); 1.992(2.1); 1.913 (0.7); 1.231 (0.8); 1.195 (0.6); 1.177 (1.1); 1.159 (0.6);0.008 (3.0); 0.000 (67.1); −0.150 (0.3) II-4 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 8.056(0.3); 8.039(8.3); 8.033(8.6);7.642(0.3); 7.636(0.4); 7.600(8.8); 7.594(8.8); 7.259(0.6); 7.192(16.0);5.761(0.7); 3.914(1.7); 3.377(0.3); 3.339(0.5); 3.173(0.5); 2.530(0.5);2.526(0.8); 2.517(12.0); 2.512(25.0); 2.508(33.6); 2.503(25.3);2.499(12.9); 2.090(0.6); 1.992(0.6); 1.228(0.6); 1.178(0.4); 0.008(1.0);0.000(30.9); −0.009(1.3) II-5 ¹H-NMR, Solvent [D₆]-DMSO, spectrometer:399.95 MHz: δ = 13.246(0.7); 9.436(8.9); 8.009(6.9); 7.985(7.4);7.542(6.6); 7.539(6.4); 7.519(5.9); 7.516(5.8); 7.223(16.0); 6.631(1.3);6.457(0.4); 5.949(0.3); 5.759(0.5); 3.915(1.1); 3.392(0.4); 3.338(4.7);2.680(0.4); 2.676(0.5); 2.511(60.9); 2.507(77.5); 2.503(58.8);2.422(1.1); 2.338(0.5); 2.334(0.6); 2.089(0.9); 1.992(0.5); 1.913(1.1);0.939(0.5); 0.007(2.8); 0.000(51.8) II-6 ¹H-NMR, Solvent [D₆]-DMSO,spectrometer: 399.95 MHz: δ = 13.290(0.6); 8.146(4.9); 8.124(5.0);7.716(4.6); 7.698(5.3); 7.465(3.5); 7.443(4.0); 7.425(2.9); 7.394(0.5);7.318(16.0); 4.040(0.6); 4.022(0.6); 3.918(1.4); 3.340(3.5);2.512(35.5); 2.508(46.4); 2.503(36.0); 2.334(0.3); 1.992(2.4);1.913(1.8); 1.195(0.6); 1.177(1.3); 1.160(0.6); 0.008(1.4); 0.000(29.1)

BIOLOGICAL EXAMPLES Meloidogyne Incognita—Test

Solvent: 125.0 parts by weight of acetone

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with water to the desired concentration.

Vessels are filled with sand, a solution of the active ingredient, asuspension containing eggs and larvae of the southern root-knot nematode(Meloidogyne incognita) and salad seeds. The salad seeds germinate andthe seedlings grow. Galls develop in the roots.

After 14 days the nematicidal activity is determined on the basis of thepercentage of gall formation. 100% means no galls were found and 0%means the number of galls found on the roots of the treated plants wasequal to that in untreated control plants.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 20 ppm:I-1, I-3, I-9, I-16, I-17, I-18, I-19, I-21, I-22, I-23, I-25, I-26,I-27, I-30, I-33, I-34, I-35, I-36, I-37, I-38, I-39, I-40, I-41, I-42,I-43, I-45, I-57, I-58, I-59, I-60, I-62, I-63, I-64, I-65, I-68, I-69,I-70, I-71, I-72, I-73, I-74, I-75, I-77, I-78

In this test, for example, the following compounds from the preparationexamples showed good activity of 90% at an application rate of 20 ppm:I-2, I-3, I-4, I-5, I-8, I-9, I-10, I-12, I-14, I-15, I-20, I-29, I-30,I-32, I-44, I-46, I-49, I-51, I-52, I-66, I-67, I-76

Meloidogyne incognita—Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2.5 parts by weight of alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier and is diluted with water to the desired concentration. Inthe calculation of the concentration the soil volume has to be included.Care has to be taken that the emulsifier concentration in the soil doesnot exceed 20 ppm. Further test concentrations are prepared by dilutionwith water.

The compound solution is poured into pots filled with soil (loamy sand).A suspension containing eggs and larvae of the southern root-knotnematode (Meloidogyne incognita) is added, salad seeds are spread on thesoil surface and covered with quartz sand. The salad seeds germinate andthe seedlings grow. Galls develop on the roots.

After 21 days the nematicidal activity is determined on the basis of thepercentage of gall formation. 100% means no galls were found; 0% meansthe number of galls found on the roots of the treated plants was equalto that in untreated control plants.

In this test, for example, the following compounds from the preparationexamples showed good activity of 80% at an application rate of 8 ppm:I-47

Myzus Persicae—Spray Test

Solvent: 78.0 parts by weight acetone

-   -   1.5 parts by weight dimethylformamide

Emulsifier: alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvents and isdiluted with water, containing an emulsifier concentration of 1000 ppm,to the desired concentration. Further test concentrations are preparedby dilution with emulsifier containing water.

Chinese cabbage (Brassica pekinensis) leaf disks infected with allinstars of the green peach aphid (Myzus persicae), are sprayed with apreparation of the active ingredient of the desired concentration.

After 6 days mortality in % is determined. 100% means all aphids havebeen killed and 0% means none of the aphids have been killed.

In this test, for example, the following compounds from the preparationexamples showed good activity of 100% at an application rate of 500g/ha: I-15

In this test, for example, the following compounds from the preparationexamples showed good activity of 90% at an application rate of 500 g/ha:I-46

Tetranvechus urticae—spray test OP-resistant

Solvent: 78.0 parts by weight acetone

-   -   1.5 parts by weight dimethylformamide

Emulsifier: alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvents and isdiluted with water, containing an emulsifier concentration of 1000 ppm,to the desired concentration. Further test concentrations are preparedby dilution with emulsifier containing water.

French bean (Phaseolus vulgaris) leaf disks which are heavily infestedwith all stages of the two spotted spidermite (Tetranychus urticae), aresprayed with a preparation of the active ingredient of the desiredconcentration.

After 6 days mortality in % is determined. 100% means all spider miteshave been killed and 0% means none of the spider mites have been killed.

In this test, for example, the following compounds from the preparationexamples showed good activity of 85% at an application rate of 500 g/ha:I-15

What is claimed:
 1. A compound of the formula (II-1):


2. A compound of the formula (II-2):


3. A compound of the formula (II-4):


4. A compound of the formula (II-5):


5. A compound of the formula (II-6):